3-(Trifluoromethyl)benzylamine → 2-Chloro-3-phenoxy-6-nitro-N-(3-trifluoromethyl-benzyl)-aniline

HRID 1902597Notes

Reaction equation

[Cl:1][C:2]1[C:7](OC2C=CC=CC=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31]>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH:31][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27]([C:26]([F:25])([F:35])[F:36])[CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3.41 gm of 2-chloro-4-nitro-1,3-diphenoxy-benzene, 5 ml of dioxane and 4 gm of 3-trifluoromethyl-benzylamine was stirred for 12 hours at 100° C. Thereafter, the reaction mixture was evaporated, the residue was taken up in chloroform, the resulting solution was extracted first with 2 N sodium hydroxide and then with 2 N hydrochloric acid, and the organic phase was dried with sodium sulfate. The chloroform was distilled off, leaving 4.0 gm (95% of theory) of the title compound as a viscous yellow oil.

Workup

customThereafter, the reaction mixture was evaporated
extractionthe resulting solution was extracted first with 2 N sodium hydroxide
dry with materialwith 2 N hydrochloric acid, and the organic phase was dried with sodium sulfate
distillationThe chloroform was distilled off

Sources & evidence

ORD record: ord-da6025370c7349b69d2286c30b7edc35
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364875

Reaction notes

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