Pyrrole-2-Carboxylic Acid → beta-Oxo-alpha-(phenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile
Reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].CC(C)([O-])C.[K+].[NH:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](O)=[O:25].P(C#N)(=O)(OCC)OCC>CN(C)C=O.O>[O:25]=[C:24]([C:20]1[NH:19][CH:23]=[CH:22][CH:21]=1)[CH:3]([C:4](=[O:5])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
to a solution of 1.6 g of α-cyanoacetanilide in 10 ml of dimethylformamide is added 3.4 g of potassium t-butoxide. The stirred cooled suspension is treated with a solution of 1.1 g of pyrrole-2-carboxylic acid and 1.4 ml of diethyl phosphorocyanidate in 6 ml of dimethylformamide. After standing for one half hour, solution is treated with 80 ml of cold water, filtered and acidified with 6N hydrochloric acid. The suspended product is collected, washed with water, dried, and dissolved in ethyl acetate. The ethyl acetate solution is filtered and evaporated to dryness. Recrystallization from ether-ethanol yields β-oxo-α-(phenylcarbamoyl)-β-(2-pyrrolyl)-propionitrile of Example 1.
Workup
- temperatureThe stirred cooled suspension
- waitAfter standing for one half hour
- filtrationfiltered
- customThe suspended product is collected
- washwashed with water
- customdried
- dissolutiondissolved in ethyl acetate
- filtrationThe ethyl acetate solution is filtered
- customevaporated to dryness
- customRecrystallization from ether-ethanol
Sources & evidence
- ORD record
- ord-b292133de2964c528d6c4406c7bce408
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04644010
Reaction notes
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