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Synthesis of substituted Amidoundecanoic acids Chapter 2

70

2.1 Introduction

Oleochemistry is a fascinating interdisciplinary subject, and it has become

more so, since the discovery of unusual fatty acids from minor-oilseeds and their

derivatization leads to industrially important and biologically active novel

oleochemicals. It is also dealt with the synthesis of fatty acid(s) derivatives and

a special strength of oleochemical industries which have generated the valuable

products from non-edible oils or lower quality fats. On the other aspect,

currently it is represented as one of the major possibilities within the big

challenge of chemistry of renewable products as a biodiesel. Thus, it is an

important branch of chemistry and privileged part in organic chemistry,

medicinal chemistry and polymer chemistry, encompassing the diverse range of

biological and industrial applications. It is used in the making of soaps, now it

is found in a wide variety of sectors like food industries, cosmetics industries,

pharmaceutical industries, oleochemical industries and polymer industries. It

offers a variety of possibilities to produce well-known and new products based

on renewable raw materials. 1-3

The larger amounts of oils and fats are transformed by chemical reaction

into basic fatty materials for use in the important oil-based industries. Many

oleochemicals are manufactured starting with normal fatty acids and unusual

fatty acids and their corresponding derivatization. Thus, oleochemicals are

often categorized into basic oleochemicals such as fatty acids, fatty methyl

esters, fatty alcohols, fatty amines and glycerol, and their further downstream

derivatives obtained from further chemical modifications of these basic

oleochemicals. Such oleochemicals exhibit interesting properties such as


71

excellent emolliency, surface activity, emulsifying properties as well as

beneficial biological properties. As such, these compounds find many

applications in cosmetics, pharmaceuticals, food and other chemical

industries.4-6

During the past decade, production and utilization of oleochemicals

have grown in size and diversity. Thus, new and interesting novel

oleochemicals are being exploited for industrial utilization. Therefore, these

fat-derived oleochemicals are essential to a variety of industrial areas such as

coatings, surfactants, plasticizers, lubricant additives (antislip and antiblock

additives), cosmetics, pharmaceuticals, soaps, detergents, textiles, plastics, and

organic pesticides. In the industrial field, there has been competition between

oleochemicals and petrochemicals. The ever-increasing cost of petrochemicals

has diverted the attention of chemists to the synthesis of new oleochemicals

derived from natural fatty acids.7-9

Amide bond linkage is a worldwide and important core structure in

pharmaceutical, chemical, and many natural products. Many procedures for the

formation of amides are known in the literature. The most common methods

are the reaction between carboxylic acid derivatives particularly acid halides,

acid anhydrides, and esters with the amines.10-12 Despite their wide scope,

limitations are associated with the use of acid halides, anhydrides, and esters.

Limitations are mostly due to the limited stability of many acid chlorides and

the need for preparation of hazardous reagents (thionyl chlorides, etc.), which

release corrosive and volatile byproducts.13-15 Reactions with esters require


72

strongly basic or acidic catalysts.16,17 Thus, the reaction between double bond

of fatty acids with nitriles in the presence of mineral acids such as sulfuric acid

(Ritter reaction) for the preparation of substituted amido-fatty acids has been

preferred.18-20

Fatty acid amides are of considerable interest due to their wide range of

application in lubricants, surfactants, cosmetics, shampoo, detergents,

photographic materials, polyolefin foaming materials, polymer stabilizers,

photocurable developers, and pigments.21-27 They have been prepared by

reaction of fatty acids with anhydrous ammonia under high temperature

(200oC) and high pressure.28 In this procedure, an additional purification step is

also required to obtain pure fatty amide. To overcome these drawbacks,

enzymatic synthesis offers potential alternative processes.29-32 However, in

their preparation procedures primary fatty amides such as oleamide from oleic

acid and erucamide from erucic acid have been prepared as the main products.

On the other hand, fatty acid amides represent a class of

neuromodulatory lipids that includes the endocannabinoid anandamide and the

sleep-inducing substance oleamide.33-38 Therefore, amidation of fatty acids

imparts a broad spectrum of activity against bacteria, yeasts, and molds. Due to

enhanced functionality and significant bioactive properties in secondary fatty

amides, there is an increasing interest in their production and characterization.39


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2.2 Recent Methods for the synthesis of Amido-acid derivatives

H3C CH2 CH CH CH2 COOH77

+ RCNH3C CH2

HC CH2 yxNHC OR

H2SO4 OH

O

x + y = 15Substituted amidostearic fatty acid derivatives

R = Different nitriles

The important reported methods have been listed in this study as

follows-

E.T. Roe and D. Swern18 reported addition of acetonitrile, propionitrile,

acrylonitrile, benzonitrile, cyanoacetic acid, malononitrile and succinonitrile to

the double bond of oleic acid in sulfuric acid solution gives good yields of

substituted amidostearic fatty acids. Amidostearic acid shows typical amino

acid properties which can be prepared in excellent yield from acetamido stearic

acid by hydrolysis with aqueous sulphuric acid.

E.T. Roe and D. Swern19 reported that the liquid hydrogen cyanide has

been added to the double bonds of oleic acid, ricinoleic acid and undecylenic

acid in 85-90% sulfuric acid to give good yields of formamidostearic acid,

hydroxyformarnidostearic acid and formamidoundecanoic acid, respectively.

These can be converted into the corresponding free amino fatty acids by

neutrilization.

R CH CH R'HCN/H2SO4

20 - 30oCR

HC

HC R'

H NHHC O

NaOH

HClR

HC

HC R'

H NH2

Amino fatty acidsAmido fatty acidsR = (CH2)7 CH3 & R' = (CH2)7 COOH [Oleic acid]

CH2HCOH

(CH2)5 CH3 & R' = (CH2)7 COOH [Ricinoleic acid]

H

R =

R = & R' = (CH2)8 COOH [Undecylenic acid]


74

E.T. Roe20 and others have synthesized the addition of substituted

phenols and phenyl ethers to the double bond of oleic acid in the presence

carbonium ion producing reagents such as 95% sulfuric acid solution or resin

catalyst gave good yields of methyl esters of substituted phenyl stearic acids.

H3C CH2 CH CH CH2 COOCH377

H3C CH2HC CH2 yxR

95% H2SO4

OCH3

O

x + y = 15R = Substituted phenols & phenylethers

or Resin catalyst

Methyl esters of substituted phenyl stearic acids

K.M. Hosamani and S.K. Hosamani40 have reported novel route for the

synthesis of substituted amidoundecanoic acids via Amido-Imido1

Tautomerization by acid-catalyzed addition of nitriles to undec-10-enoic acid.

K. M. Hosamani and R.S. Pattanashettar41 have reported synthesis of

novel N,N-bis(1-carboxy-15-hydroxy-n-pentadec-8-yl)alkyl or -aryl diamides

by the reaction of different nitriles with ambrettoleic acid. The specific nitriles

malononitrile, succinonitrile, glutaronitrile, adiponitrile, pimelonitrile,

suberonitrile azelanitrile, and 1,2-dicyanobenzene were added to the double

bond of ambrettoleic acid in the presence of con. sulfuric acid, and the resulting

reaction mixture was then hydrolyzed to yield the substituted diamides.


75

K.M. Hosamani and R.M. Sattigeri85 have synthesized a series of novel

9-[substituted amido]-16-ol-hexadecanoic acids by the reaction of different

nitriles with 16-hydroxyhexadec-cis-9-enoic acid.

Y. Terada43 and others have reported the amidation of aliphatic fatty

acids with long-chain aliphatic amines using multivalent metal salts, such as

ferric chloride and sulfate as a catalyst.

M. Musteata44 and others have reported acylation of different amino

derivatives under green conditions with oleic acid or tail oil fatty acids.


76

A. Yildirim and M. Cetin45 reported synthesis of long-chain N-alkyl-2-

(phenylthio)acetohydrazides via the reactions of 2-(phenylthio) acetohydrazide

with long-straight-chain aldehydes and then reduction with sodium borohydride

to give 2-oxo-2-phenylethyl-2-alkanoyl hydrazine carbodithioates.


77

2.3 Present work

The primary aim of the present work is to carry out the synthesis of

novel substituted amidoundecanoic acid derivatives (Scheme-1) via Amido-

Imidol tautomerization, which involves reaction between undecylenic acid and

mono-nitriles in the presence of sulfuric acid below 8oC. The newly

synthesized compounds are obtained in good to excellent yield. Thus, the

unusual fatty acids are highly important to the oleochemical industries as raw

materials for the production of a variety of oleochemicals for industrially

important and biological active compounds.

Scheme-1.

CH3

CH3 CH3

CH3,

H3C

CH3

CH3CH3

CH3

R = a)

j)

b) , ,c) d)

e) , f) , g)

h) , i) ; and

Where

Considering the extensive applications of amide-linkage containing

oleochemicals such as substituted amidoundecanoic acids, these are being

exploited for industrial utilization and also for pharmaceutical purposes. In the

summary, it is reported that the synthesis of a series of substituted

amidoundecanoic acids using different mono-nitriles in the presence of strong

sulfuric acid yielding potent compounds.


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2.4 Experimental procedure

2.5 Results and discussion

A homogenous mixture of undecylenic acid (0.01 mole) and different

mono-nitriles (0.03 mole) in a dropping funnel was added in 30 min to conc.

H2SO4 (0.06 mole) in a three necked RB flask fitted with a thermometer and an

efficient stirrer. The temperature was maintained below 8oC by external

cooling. After complete addition, the reaction mixture was stirred for 24 h and

poured into ice-cold water. The soft syrupy insoluble mass was stirred

occasionally and then allowed to stand overnight in dilute acidic medium.

Continue the stirring until the product had hardened to a crumbly wax. The

product was washed thoroughly with distilled water and dried.

In present study, the newly synthesized substituted amidoundecanoic

acid from undecylenic acid and different mono-nitriles in the presence of

sulfuric acid medium is described. The reaction sequences employed for the

synthesis of target compounds are given in Schemes-1. The analytical data and

their physical properties are given in Table-1. Mechanistically, sulfuric acid

first adds to the double bond of undecylenic acid to form sulfate ester followed

by the reaction of this intermediate with the different mono-nitriles (Scheme-

2).40 It may be significant that, when the reaction mixture is poured into ice-

cold water to isolate the product, an oily material is obtained. The viscous, oily

mass requires time to hydrolyze and undergo Amido-Imidol tautomerization to

the solid amide, to form the actual product. All the synthesized compounds

were characterized by IR, 1H NMR, 13C NMR, Mass and Elemental analysis.


79

Scheme-1.1. Plausible reaction Mechanism

Table-1. Synthesis of substituted Amidoundecanoic acidsa

Entry

Mono-nitriles

Product Time (h)b

Yield (%)c

1 Acetonitrile 1a

16 95

2 Benzonitrile 1b

15 79

3 Benzylcyanide 1c

18 64

4 Propionitrile 1d

22 80

5 Butyronitrile 1e

26 88

6 Valeronitrile

1f

21 76

7 o-tolunitrile 1g

17 83

8 m-tolunitrile 1h

16 79

9 p-tolunitrile 1i

23 75

10 Isobutyronitrile 1j

21 77

a Reaction conditions: Substituted mono-nitriles (0.01 mol), undecanoic acid (0.01 mol). b Time to finish the reaction monitored by TLC. c Yield refer to isolated products.


80

The IR spectra of all the compounds (1a -1j) showed strong absorption

bands in the range of 3405–3428cm-1 and 3238–3265 cm-1 for OH and NH

stretching. The C=O stretching for carboxylic acid and NH–C=O were

observed around 1701–1712 and 1637–1660 cm-1 respectively. The 1H NMR

spectra indicated the chemical shift of the NH proton around 5.85–6.31 ppm as

singlet peak, assigned to the NH proton. Similarly, a broad singlet in the range

11-12 ppm for COOH, disappeared on D2O addition. 13C NMR spectral data

for the title compounds most characteristic peak around δ 173–175ppm for and

165–170ppm (CONH) indicated the formation of carbonyl-amide linkage. The

mass spectrum of the entire compounds showed molecular ion peak, which is

in agreement with the molecular formula.

The structures of newly synthesized substituted amidoundecanoic acids

(1a -1j) were supported by IR, 1H NMR, 13C NMR and Mass spectrometry.

10-acetamidoundecanoic acid (1a) :

IR (KBr): (vmax/cm-1): 3407, 3258, 2930

2851, 1712, 1639; 1H NMR (300 MHz,

DMSO) δ (ppm) 1.04 (d, 3H, CH3), 1.26 (bs,

12H, (–CH2–)6), 1.65(d, 2H, CH2), 1.94 (s, 3H, CH3), 2.34 (t, 2H, CH2–

COOH), 3.98–4.1 (m, 1H, CH), 6.24 (s, 1H, NH), 11.9 (s, 1H, COOH). 13C

NMR (75 MHz, DMSO) δ 22.35, 24.22, 25.33, 27.62, 28.17, 28.29, 29.35,

29.55, 29.69, 31.43, 34.52, 36.78, 45.36, 50.52, 165.48, 173.19. LC-MS: m/z

243 (M). Anal. Calcd. For C13H25NO3: C, 64.16; H, 10.36; N 5.76%, Found: C,

64.22; H, 10.32; N, 5.79%.

H3CCH

OH

O

NHCO

H3C


81

10-benzamidoundecanoic acid (1b) :

IR (KBr): (vmax/cm-1): 3419, 3243, 2921,

2848, 1708, 1643; 1H NMR (300 MHz,

DMSO) δ (ppm) 1.02 (d, 3H, CH3), 1.29

(bs, 12H, (–CH2–)6), 1.46 (s, 2H, CH2), 2.15–2.19 (s, 2H, CH2–COOH), 3.66–

3.82 (m, 1H, CH), 6.01 (br, 1H, NH) 7.74–7.88 (m, 5H, Ar–H), 11.96 (s, 1H,

COOH). 13C NMR (75 MHz, DMSO) δ 21.63, 23.54, 25.34, 26.23, 26.47,

28.22, 29.38, 29.58, 29.73, 31.52, 34.51, 36.96, 44.87, 50.33, 115.51, 118.25,

135.63, 169.4, 175.34; LC-MS: m/z 305 (M+). Anal. Calcd. For C18H27NO3: C,

70.79; H, 8.91; N 4.59%, Found: C, 70.84; H, 8.95; N, 4.52%.

10-(2-phenylacetamido)undecanoic acid (1c) :

IR (KBr): (vmax/cm-1): 3415, 3248,

2925, 2845, 1704, 1652; 1H NMR (300

MHz, DMSO) δ (ppm) 1.01 (s, 3H,

CH3), 1.26 (s, 12H, (–CH2–)6), 1.78 (s, 2H, CH2), 2.23 (t, 2H, CH2–COOH),

3.21 (s, 2H, CH2), 3.59–3.8 (m, 1H, CH), 6.36 (s, 1H, NH), 7.39–7.51 (m, 5H,

Ar–H), 11.93 (s, 1H, COOH). LC-MS: m/z 319 (M). Anal. Calcd. For

C19H29NO3: C, 71.44; H, 9.15; N 4.38%, Found: C, 71.48; H, 9.10; N, 4.45%.

H3CCH

OH

O

NHCO

H3CCH

OH

O

NHCO


82

10-propionamidoundecanioc acid (1d) :

IR (KBr): (vmax/cm-1): 3412, 3258, 2917,

2856, 1701, 1660; 1H NMR (300 MHz,

DMSO) δ (ppm) 0.95 (s, 3H, CH3), 1.04 (d,

3H, CH3), 1.24 (s, 12H, (–CH2–)6), 1.61 (s, 2H, CH2), 2.19 (s, 2H, O=C–CH2),

2.32 (s, 2H, CH2–COOH), 3.88–4.09 (S, 1H, CH), 5.93 (br, 1H, CONH), 11.58

(s, 1H, COOH). LC-MS: m/z 258 (M+). Anal. Calcd. For C14H27NO3: C, 65.33;

H, 10.57; N 5.44%, Found: C, 65.29; H, 10.62; N, 5.38%.

10-butyramidoundecanoic acid (1e) :

IR (KBr): (vmax/cm-1): 3405, 3245, 2929,

2856, 1707, 1644; 1H NMR (300 MHz,

DMSO) δ (ppm) 0.98 (t, 3H, CH3), 1.14 (d,

3H, CH3), 1.30 (s, 12H, (–CH2–)6), 1.41 (s, 2H, CH2), 1.65–171 (m, 2H, CH2),

2.13 (t, 2H, O=C–CH2), 2.33 (t, 2H, CH2–COOH), 3.98–4.03 (m, 1H, CH),

6.08 (br, 1H, CONH) 11.62 (s, 1H, COOH). LC-MS: m/z 271 (M). Anal.

Calcd. For C15H29NO3: C, 66.38; H, 10.77; N 5.16%, Found: C, 66.35; H,

10.80; N, 5.21%.

H3CCH

OH

O

NHCO

H3CCH

OH

O

NHCO


83

10-Pentanamidoundecanoic acid (1f) :

IR (KBr): (vmax/cm-1): 3422, 3238, 2931,

2858, 1711, 1642; 1H NMR (300 MHz,

DMSO) δ (ppm) 0.96 (s, 3H, CH3), 1.12 (d,

3H, CH3), 1.32 (s, 12H, (–CH2–)6), 1.62 (s,

2H, CH2), 1.66 (d, 4H, CH2), 2.14 (s, 2H, O=C–CH2), 2.32 (t, 2H, CH2–

COOH), 3.98–4.0 (S, 1H, CH), 5.85 (br, 1H, CONH) 11.8 (s, 1H, COOH). LC-

MS: m/z 286 (M+). Anal. Calcd. For C16H31NO3: C, 67.33; H, 10.95; N 4.91%,

Found: C, 67.38; H, 11.00; N, 4.87%.

10-(2-methylbenzamido)undecanoic acid (1g) :

IR (KBr): (vmax/cm-1): 3425, 3258, 2924,

2855, 1703, 1657; 1H NMR (300 MHz,

DMSO) δ (ppm) 1.21 (s, 3H, CH3), 1.31

(s, 12H, (–CH2–)6), 1.63 (s, 2H, CH2), 2.32 (s, 2H, CH2–COOH), 2.42 (s, 3H,

Ar–CH3), 3.82–4.07 (m, 1H, CH), 6.28 (br, 1H, CONH), 7.43–7.71 (m, 4H,

Ar–H) 11.4 (s, 1H, COOH). LC-MS: m/z 319 (M). Anal. Calcd. For


H3CCH

OH

O

NHCO

H3CCH

OH

O

NHCO


84

10-(3-methylbenzamido)undecanoic acid (1h) :

IR (KBr): (vmax/cm-1): 3408, 3254,

2926, 2853, 1704, 1637; 1H NMR (300

MHz, DMSO) δ (ppm) 1.22 (s, 3H,

CH3), 1.31 (s, 12H, (–CH2–)6), 1.56 (s, 2H, CH2), 2.36 (s, 2H, CH2–COOH),

2.42 (s, 3H, Ar–CH3), 3.82–4.06 (S, 1H, CH), 6.24 (br, 1H, CONH), 7.34 (t,

1H, Ar-H), 7.42 (d, 1H, Ar-H), 7.72 (s, 1H, Ar-H), 7.88 (d, 1H, Ar-H), 11.61

(s, 1H, COOH). LC-MS: m/z 320 (M+). Anal. Calcd. For C19H29NO3: 71.44; H,

9.15; N 4.38%, Found: C, 71.41; H, 9.29; N, 4.41%.

10-(4-methylbenzamido)undecanoic acid (1i) :

IR (KBr): (vmax/cm-1): 3415, 3265,

2925, 2852, 1708, 1651; 1H NMR (300

MHz, DMSO) δ (ppm) 1.19 (d, 3H,

CH3), 1.29 (s, 12H, (–CH2–)6), 1.54 (s, 2H, CH2), 2.30 (s, 2H, CH2–COOH),

2.35 (s, 3H, Ar–CH3), 3.89–3.99 (S, 1H, CH), 6.2 (br, 1H, CONH), 7.27–7.69

(m, 4H, Ar–H) 11.68 (s, 1H, COOH). LC-MS: m/z 320 (M). Anal. Calcd For


H3CCH

OH

O

NHCO

H3CCH

OH

O

NHCO


85

10-isobutyramidoundecanoic acid (1j) :

IR (KBr): (vmax/cm-1): 3428, 3259, 2928,

2854, 1712, 1649; 1H NMR (300 MHz,

DMSO) δ (ppm) 1.1 (s, 6H, CH3), 1.18 (s,

3H, CH3), 1.29 (s, 12H, (–CH2–)6), 1.51 (d, 2H, CH2), 2.24 (s, 1H, CH of

CONH), 2.35 (s, 2H, CH2–COOH), 3.89 (S, 1H, CH), 6.31 (br, 1H, CONH)

11.86 (s, 1H, COOH). LC-MS: m/z 271 (M). Anal. Calcd. For C15H29NO3: C,

66.38; H, 10.77; N 5.16%, Found: C, 66.35; H, 10.81; N, 5.19%.

H3CCH

OH

O

NHCO


86

Spectrum 1: IR Spectrum of compound 1b

CH3

HC

OH

ONH

C

O

Spectrum 3: 1H NMR Spectrum of compound 1b in DMSO


87

CH3

HC

OH

ONH

C

O

Spectrum 3: 1H NMR Spectrum of compound 1b (expansion)

CH3

HC

OH

ONH

C

O

Spectrum 3: 13C NMR Spectrum of compound 1b in DMSO


88

CH3

HC

OH

O

NHC

O

(m/z, 305)

Spectrum 4: Mass Spectrum of compound 1b


89

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