Hydrochloric Acid → 2,4-Dinitro-N-(2,4,6-trichlorophenyl)-6-(trifluoromethyl)aniline

HRID 1764732Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[H-].[Na+].Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[CH:16][C:15]=1[C:26]([F:29])([F:28])[F:27].Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH:4][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[CH:16][C:15]=1[C:26]([F:27])([F:29])[F:28]

Participants

Conditions

Temperature: 10 °C

Procedure

2,4,6-trichloroaniline (3.9 g.) was dissolved in dimethylformamide (20 ml.) and carefully added to sodium hydride (obtained by washing sodium hydride in mineral oil (2.0 g; 50%) with petrol) suspended in dimethylformamide (10 ml.) at 10° C. When the addition was complete the temperature of the mixture was allowed to rise to the ambient temperature over a period of 30 minutes, before being cooled to 10° C. A solution of 2-chloro-3,5-dinitrobenzotrifluoride (5.4 g.) in dimethylformamide (20 ml.) was slowly added, and the mixture stirred at the ambient temperature for 5 hours, and allowed to stand for further 16 hours. The mixture was poured into iced water and the resultant mixture acidified with concentrated hydrochloric acid. The precipitate was collected by decanting off the supernatant liquid and recrystallised from methylated spirit to yield 2(2,4,6-trichloroanilino)-3,5-dinitrobenzotrifluoride, melting point 105° C.

Workup

additionWhen the addition
waitto stand for further 16 hours
customThe precipitate was collected
customby decanting off the supernatant liquid
customrecrystallised from methylated spirit

Sources & evidence

ORD record: ord-f990473f50ae4a62b4ed77589e0e79b1
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04117167

Reaction notes

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