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

HRID 1109671Notes

Reaction equation

HRID 1109671 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. 1HNMR (CDCl3) (90 MHz) 1.37 (s, 9H), 2.08 (s, 3H), 2.66 (dd, 1H), 3.06 (dd, 1H), 2.80 (s, 3H) 3.82 (dd, 1H) 4.02 (exchangeable s, 2H), 7.15 (meta d, 2H).

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-f11ea1a357b94536bc926473530edda0
Source dataset
uspto-grants-1994_06
Patent number
US05321067

Reaction notes

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