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

HRID 1885805Notes

Reaction equation

HRID 1885805 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].[CH3:14][N:15]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]1=[O:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:14][N:15]1[C:19](=[O:20])[CH2:18][CH:17]([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:16]1=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70261N-MethylmaleimideHCID 153245012-Tert-butyl-4-mercapto-6-methylaniline

Product 1

HCID 15324505N-methyl-2-(4-amino-3-tert-butyl-5-methylphenylthio)succinimideYield 52.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 1.0 g (5 mmol) of 2-tert-butyl-4-mercapto-6-methylaniline, 0.6 g (5 mmol) of N-methylmaleimide and 0.1 g (1 mmol) of triethylamine in 10 mL of toluene is heated at 50° C. for 18 hours. The solvent is removed in vacuo and the residue is purified by flash chromatography (silica gel, 3:2, heptane:ethyl acetate eluent) followed by recrystallization from a heptane:toluene solvent mixture to give 0.8 g (51%) of the title compound as a white solid melting at 92°-94° C.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by flash chromatography (silica gel, 3:2, heptane:ethyl acetate eluent)
  3. customfollowed by recrystallization from a heptane

Sources & evidence

ORD record
ord-5e14519550e2483aa49232a3c0627d8b
Source dataset
uspto-grants-1992_09
Patent number
US05145970

Reaction notes

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