Hydrochloric Acid → 3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile
Reaction equation
[H-].[Na+].[NH2:3][CH:4]=[CH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8].CO[CH:14]=[CH:15][C:16]#[N:17].Cl>CN(C)C=O.O>[F:8][C:7]([F:10])([F:9])[C:6](=[O:11])[CH:5]=[CH:4][NH:3][CH:14]=[CH:15][C:16]#[N:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium hydride (60% dispersion in mineral oil suspension, 4.00 g, 100 mmol) was added and washed with hexane twice. Into this flask, N,N-dimethylformamide (100 ml) was added and then a solution prepared by dissolving 4-amino-1,1,1-trifluoro-3-buten-2-one (13.9 g, 100 mmol) and 3-methoxyacrylonitrile (8.30 g, 100 mmol) in N,N-dimethylformamide (50 ml) was added dropwise under ice-cooling. After stirring the mixture at room temperature for 3 hours, the reaction mixture was poured into water (500 ml). This mixture was acidified with concentrated hydrochloric acid under ice-cooling, the precipitate was collected by filtration and then washed with cold water. The obtained precipitate was dried under reduced pressure to obtain 8.20 g (yield 43.1%) of a mixture of compounds (IIa) and (IIb).
Workup
- washwashed with hexane twice
- additionInto this flask, N,N-dimethylformamide (100 ml) was added
- customa solution prepared
- additionwas added dropwise under ice-
- temperaturecooling
- temperaturecooling
- filtrationthe precipitate was collected by filtration
- washwashed with cold water
- customThe obtained precipitate was dried under reduced pressure
Sources & evidence
- ORD record
- ord-47c6e9f6f17f48a4a4c1d9deed46e6b9
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07015236B2
Reaction notes
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