4-Chlorobenzylamine → 2-Chloro-3-phenoxy-6-nitro-N-(4-chloro-benzyl)-aniline

HRID 1902596Notes

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.[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>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][C:26]([Cl:25])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5 gm of 2-chloro-4-nitro-1,3-diphenoxy-benzene, 10 ml of dioxane and 6 gm of 4-chlorobenzylamine was stirred for 12 hours at 80° C. Thereafter, the reaction mixture was evaporated, the residue was taken up in chloroform, the resulting solution was extracted with 1 N sodium hydroxide, and the organic phase was dried with sodium sulfate. The chloroform was distilled off, and the residue was recrystallized from ethanol, yielding 4.7 gm (82.7% of theory) of the title compound, m.p. 95°-96° C.

Workup

customThereafter, the reaction mixture was evaporated
extractionthe resulting solution was extracted with 1 N sodium hydroxide
dry with materialthe organic phase was dried with sodium sulfate
distillationThe chloroform was distilled off
customthe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-95f192373adf4dd7a632ed674995a2da
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364875

Reaction notes

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