2,6-Di-tert-butyl-4-mercaptophenol → N-Cyclohexyl-2-(3,5-di-tert-butyl-4-hydroxyphenylthio)-succinimide

HRID 1263311Notes

Reaction equation

HRID 1263311 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([N:23]2[C:27](=[O:28])[CH:26]=[CH:25][C:24]2=[O:29])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(N(CC)CC)C>[CH:17]1([N:23]2[C:27](=[O:28])[CH2:26][CH:25]([S:11][C:9]3[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=3)[C:24]2=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 742031H-Pyrrole-2,5-dione, 1-cyclohexyl-

Product 1

HCID 13547661N-Cyclohexyl-2-(3,5-di-tert-butyl-4-hydroxyphenylthio)-succinimideYield 50.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The procedure of Example 1 is repeated using 11.95 grams of 2,6-di-tert-butyl-4-mercaptophenol, 8.96 grams of N-cyclohexylmaleimide, and 0.5 grams of triethylamine. The residue is recrystallized from a heptane-toluene mixture to give 10.5 grams of a white solid, m.p. 94°-98° C.

Workup

  1. customThe residue is recrystallized from a heptane-toluene mixture

Sources & evidence

ORD record
ord-f086d566e657454683c8b5140491af58
Source dataset
uspto-grants-1984_06
Patent number
US04456716

Reaction notes

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