Hydrochloric Acid → 3-[4-Cyano-3-nitrophenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[C-:7]#[N:8].[K+].F[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:18]2=[O:28])=[CH:13][C:12]=1[N+:29]([O-:31])=[O:30].Cl.C#N>CN(C)C=O.O>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:18]2=[O:28])=[CH:13][C:12]=1[N+:29]([O-:31])=[O:30])#[N:8]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Potassium carbonate (16.6 g) and potassium cyanide (7.8 g) were added to a solution of 3-[4-fluoro-3-nitrophenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (31.9 g) in 250 ml of anhydrous N,N-dimethylformamide. The reaction mixture was subsequently stirred for a total of 45 hours at 75-80° C., with two further additions of potassium cyanide (in total 4.6 g) since the reaction had not proceeded completely. For working-up, water (250 ml) was added to the reaction mixture after it had cooled. The pH was subsequently brought to 2-3 by adding 60 ml of 1 N. hydrochloric acid. After nitrogen had been passed through the mixture for 4 hours to expel the hydrocyanic acid which had been liberated, the precipitate formed was separated off, washed with water and petroleum ether and dried. Yield: 17.0 g; m.p.: 135° C.
Workup
- temperaturehad cooled
- additionby adding 60 ml of 1 N
- customthe precipitate formed
- customwas separated off
- washwashed with water and petroleum ether
- customdried
Sources & evidence
- ORD record
- ord-c742b1c5b30a4ee78aaff6c4abc16244
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06656884B2
Reaction notes
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