1-Heptadecanol → 4-Heptadecyloxycarbonyl-2-nitroaniline

HRID 728406

Reaction equation

HRID 728406 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].CN(C1C=CC=CN=1)C>ClCCl>[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([O:13][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 150761-HeptadecanolHCID 218852-DimethylaminopyridineHCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 198239524-Heptadecyloxycarbonyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-nitro-4-carboxyaniline (0.52 g), heptadecanol (0.7 g) and dimethylaminopyridine (20 mg) in dichloromethane (20 ml) was prepared and dicyclohexyldicarbodiimide (0.62 g) was added. The mixture was stirred for 48 hours and filtered. After separating between chloroform and 3% caustic soda solution the organic phase was washed with water, dried with magnesium sulphate and the solvent removed to leave a yellow solid. The solid was purified by chromatography to give a yellow solid which was recrystallised from 50:50 chloroform-hexane (yield: 0.85 g, m.p. 103°-105° C.).

Workup

  1. customwas prepared
  2. filtrationfiltered
  3. customAfter separating between chloroform and 3% caustic soda solution the organic phase
  4. washwas washed with water
  5. dry with materialdried with magnesium sulphate
  6. customthe solvent removed
  7. customto leave a yellow solid
  8. customThe solid was purified by chromatography
  9. customto give a yellow solid which
  10. customwas recrystallised from 50:50 chloroform-hexane (yield: 0.85 g, m.p. 103°-105° C.)

Sources & evidence

ORD record
ord-5f8ed30fdc3d4ee4b3f7cfd705ea5317
Source dataset
uspto-grants-1991_09
Patent number
US05047516

Linked notes

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