4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

HRID 967890

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[N+:14]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[CH3:24])[NH2:20])([O-:16])=[O:15]>N1C=CC=CC=1>[CH3:24][C:23]1[CH:22]=[CH:21][C:19]([NH:20][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)=[CH:18][C:17]=1[N+:14]([O-:16])=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-trifluoromethylbenzoyl chloride (9.9 ml), 3-nitro-4-methylaniline (10 g) and pyridine (100 ml) was stirred and heated to 80° C. for 2 hours. The reaction mixture was evaporated and the residue was triturated under 2N aqueous hydrochloric acid solution. The solid so obtained was isolated, washed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane and dried under vacuum at 55° C. to give N-(4-methyl-3-nitrophenyl)-3-trifluoromethylbenzamide as a solid (21.9 g); NMR Spectrum: (DMSOd6) 7.49 (d, 1H), 7.78 (m, 1H), 7.99 (m, 2H), 8.27 (m, 2H), 8.51 (s, 1H), 10.77 (s, 1H); Mass Spectrum: M−H− 23.

Workup

customThe reaction mixture was evaporated
customthe residue was triturated under 2N aqueous hydrochloric acid solution
customThe solid so obtained
customwas isolated
washwashed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane
customdried under vacuum at 55° C.

Sources & evidence

ORD record: ord-ebeb4a8f63ed4958bd3863cb65cadbbb
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956037B2

Linked notes

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