Triethylamine → N-Octadecyl-2-(4-amino-3-tert-butyl-5-methylphenylthio)succinimide

HRID 1885804

Reaction equation

HRID 1885804 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([SH:12])[CH:9]=[C:8]([CH3:13])[C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([N:32]1[C:36](=[O:37])[CH:35]=[CH:34][C:33]1=[O:38])[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][CH2:30][CH3:31].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:14]([N:32]1[C:33](=[O:38])[CH2:34][CH:35]([S:12][C:10]2[CH:9]=[C:8]([CH3:13])[C:6]([NH2:7])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:11]=2)[C:36]1=[O:37])[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][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 871181-octadecyl-1H-pyrrole-2,5-dioneHCID 153245012-Tert-butyl-4-mercapto-6-methylaniline

Product 1

HCID 15324511N-Octadecyl-2-(4-amino-3-tert-butyl-5-methylphenylthio)succinimideYield 56.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2.8 g (14 mmol) of 2-tert-butyl-4-mercapto-6-methylaniline, 5.0 g (14 mmol) of N-octadecylmaleimide and 0.1 g (1 mmol) of triethylamine in 50 mL of toluene is heated at 50° C. for 18 hours. The solvent is removed in vacuo and the residue is purified by preparative HPLC (silica gel, 4:1, heptane:ethyl acetate eluent) to give 4.3 g (55%) of the title compound as a caramel-colored liquid.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by preparative HPLC (silica gel, 4:1, heptane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-68b54c40b3eb4d88b0dbc4f6fecd10a3
Source dataset
uspto-grants-1992_09
Patent number
US05145970

Linked notes

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