Allylamine → 2-Chloro-3-(4-cyano-phenoxy)-6-nitro-N-allyl-aniline

HRID 1902599Notes

Reaction equation

HRID 1902599 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][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1.[CH2:27]([NH2:30])[CH:28]=[CH2:29]>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=2)=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH:30][CH2:27][CH:28]=[CH2:29]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 128811532-Chloro-4-nitro-3-phenoxy-1-(4-cyano-phenoxy)-benzene

Product 1

HCID 128811652-Chloro-3-(4-cyano-phenoxy)-6-nitro-N-allyl-aniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4 gm of 2-chloro-4-nitro-3-phenoxy-1-(4-cyano-phenoxy)-benzene, 10 ml of dioxane and 2 gm of allylamine was allowed to stand at room temperature for 30 hours. Thereafter, the dioxane was distilled off, the residue was taken up in chloroform, the resulting solution was extracted with dilute sodium hydroxide, the organic phase was dried with sodium sulfate, the chloroform was distilled off, and the residue was recrystallized from ethanol. 3.5 gm (97.2% of theory) of the yellow crystalline title compound, m.p. 85°-87° C., were obtained.

Workup

  1. distillationThereafter, the dioxane was distilled off
  2. extractionthe resulting solution was extracted with dilute sodium hydroxide
  3. dry with materialthe organic phase was dried with sodium sulfate
  4. distillationthe chloroform was distilled off
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c8084c4877234fbeb0017f337ed689db
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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