4-Tert-Butylaniline → N-(4-tert-butylphenyl)-2-[[2-[(4-tert-butylphenyl)carbamoyl]phenyl]disulfanyl]benzamide

HRID 583498

Reaction equation

[C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>ClCCl.N1C=CC=CC=1>[CH3:23][C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:1](=[O:19])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][S:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:29][C:28]2[CH:30]=[CH:31][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=2)=[O:13])=[CH:30][CH:31]=1)([CH3:24])[CH3:22]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 2,2'-dithiobisbenzoyl chloride (1.20 g, 3.50 mmol) in 25 mL of dichloromethane was added to a solution of 4-tert-butylaniline (1.04 g, 6.99 mmol) in 8 mL of pyridine at 23° C. The reaction mixture was stirred for 18 hours at 23° C. under nitrogen atmosphere. The mixture was concentrated, the residue triturated with 5% aqueous HCl, and the resulting solid was collected by filtration and washed with water to yield the crude product. The crude material was recrystallized from ethyl ether-ethanol to yield 0.24 g of the title compound, mp 135-138° C.

Workup

concentrationThe mixture was concentrated
customthe residue triturated with 5% aqueous HCl
filtrationthe resulting solid was collected by filtration
washwashed with water
customto yield the crude product
customThe crude material was recrystallized from ethyl ether-ethanol

Sources & evidence

ORD record: ord-41692f4aaa7f48259f39519b8e7ff7fb
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929114

Linked notes

Loading…