Cyclopropylamine → 3-Cyclopropylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylonitrile

HRID 255956Notes

Reaction equation

HRID 255956 reaction equation
C[N:2]([CH3:18])[CH:3]=[C:4]([C:7](=[O:17])[C:8]1[CH:13]=[C:12]([F:14])[C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[C:5]#[N:6].[CH:19]1(N)C[CH2:20]1>C1(C)C=CC=CC=1>[CH:18]1([NH:2][CH:3]=[C:4]([C:7](=[O:17])[C:8]2[CH:13]=[C:12]([F:14])[C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[C:5]#[N:6])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 539967673-Dimethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylonitrile

Product 1

HCID 679449193-Cyclopropylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylonitrileYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.35 g of 3-dimethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylonitrile are refluxed with 3.2 g of cyclopropylamine and 60 ml of toluene. When the evolution of gas is finished after about 30 minutes, the toluene is removed by distillation in vacuo, and the residue is recrystallized from ethanol/light petroleum. 13.8 g of 3-cyclopropylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylonitrile of melting point 94°-95° C. are obtained.

Workup

  1. customthe toluene is removed by distillation in vacuo
  2. customthe residue is recrystallized from ethanol/light petroleum

Sources & evidence

ORD record
ord-d0c2697f1f424dbd80cd21248921cf08
Source dataset
uspto-grants-1987_10
Patent number
US04699992

Reaction notes

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