Triethylamine → beta-Oxo-alpha-(2,4-difluorophenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

HRID 236348Notes

Reaction equation

HRID 236348 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][C:9]#[N:10])=[O:7].[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N:19]=[C:20]=[O:21].CCN(CC)CC>C(COC)OC>[O:7]=[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)[CH:8]([C:20](=[O:21])[NH:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[F:11])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5932582,4-Difluorophenyl isocyanateHCID 111943553-oxo-3-(1H-pyrrol-2-yl)propanenitrile

Product 1

HCID 13370091beta-Oxo-alpha-(2,4-difluorophenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Reaction of 2.4 g of 2-pyrroloylacetonitrile with 3.1 g of 2,4-difluorophenyl isocyanate in the presence of 2.0 g Et3N in 25 ml of glyme and isolation similarly to the preceding examples, followed by trituration with and recrystallization from ethanol gives β-oxo-α-(2,4-difluorophenylcarbamoyl)-β-(2-pyrrolyl)-propionitrile, m.p. 169°-171°.

Workup

  1. customrecrystallization from ethanol

Sources & evidence

ORD record
ord-7872158a0ff5484c81ade8ebaa73e201
Source dataset
uspto-grants-1987_02
Patent number
US04644010

Reaction notes

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