Benzoyl chloride → 4,4'-Dinitrobiphenyl-2-benzamide

HRID 1377007Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6](N)[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C[N:30]1CCCC1=O>CN(C)C1C=CN=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([C:26]2[C:21]([C:20]([NH2:30])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of 4,4'-dinitro-2-biphenylamine (12.00 g, 46.29 mmol), 4-dimethylaminopyridine (5.77 g, 47.22 mmol) and N-methyl-2-pyrrolidinone (130ml) was stirred under a nitrogen atmosphere. Benzoyl chloride (9.69 g, 68.92 mmol) was added by dropping funnel at ambient temperature and the mixture heated to 160° C. and maintained at that temperature for 18 h. The resulting solution was poured into 1200 ml ice water with stirring and continued stirring overnight to give a light brown precipitate. The precipitate was filtered out and washed with water (2×100 ml), 5% sodium bicarbonate solution (2×100 ml) and water (4×200 ml) until the filtrate was clear. The crude product was dried under reduced pressure at 138° C. for 24 h to give 4,4'-dinitrobiphenyl-2-benzamide as a light brown powder (16.65 g, 99%), m.p. 242°-244° C.

Workup

customat ambient temperature
temperaturemaintained at that temperature for 18 h
stirringcontinued stirring overnight
customto give a light brown precipitate
filtrationThe precipitate was filtered out
washwashed with water (2×100 ml), 5% sodium bicarbonate solution (2×100 ml) and water (4×200 ml) until the filtrate
dry with materialThe crude product was dried under reduced pressure at 138° C. for 24 h

Sources & evidence

ORD record: ord-cc71692cfec14f08ba8f10fa2fb3b2f1
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663437

Reaction notes

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