Hydrochloric Acid → HCID 10945165, compound
Reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]C#N)=[CH:15][CH:14]=1.CC(C)([O-:25])C.[K+].OO.Cl>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[NH2:7][C:6]1[CH:8]=[C:2]([CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[C:19]([C:16]1[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=1)=[O:25]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a cold (0° C.) solution of 17.25 g (100 mmol) of 5-chloro-2-nitroaniline and 12 ml (100 mmol) of 4-fluorophenylacetonitrile in 200 ml of dimethylformamide, was added 22.44 g (200 mmol) of potassium t-butoxide, under nitrogen. The resultant reaction mixture was warmed to room temperature and reacted overnight. When the reaction was substantially complete, as indicated by TLC (eluent of 40% ethyl acetate in hexane), the reaction mixture was cooled to 0° C. followed by the addition of 30 ml of 30% hydrogen peroxide. When the reaction was substantially complete, as indicated by TLC (eluent of 40% ethyl acetate in hexane), the reaction mixture was poured into 1 liter of 1N hydrochloric acid (aqueous) which resulted in the formation of a yellow/orange precipitate. This precipitate was isolated by filtration. Yield: 23.3 g (89%).
Workup
- customThe resultant reaction mixture
- customreacted overnight
- temperaturethe reaction mixture was cooled to 0° C.
- customresulted in the formation of a yellow/orange precipitate
- customThis precipitate was isolated by filtration
Sources & evidence
- ORD record
- ord-2884574b1b7c4fca825b4e7b58ac0bb0
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05693661
Reaction notes
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