Reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1)=[O:7])#[N:4].[H-].[CH3:15][N:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21](Cl)=[O:22].Cl>COCCOC.O.CN(C)C=O>[O:22]=[C:21]([C:17]1[N:16]([CH3:15])[CH:20]=[CH:19][CH:18]=1)[CH:5]([C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1)[C:3]#[N:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To the suspension of 2.1 g of 50% NaH mineral oil (washed with petroleum ether) in 25 ml of 1,2-dimethoxyethane and 15 ml of dimethylformamide was added 6.7 g of 2-(cyanoacetylamino)thiazole. After the moderately exothermic, effervescent reaction of the hydride, there was added (swirling) a solution of N-methyl-2-pyrroloyl chloride (prepared from 2.5 g of the acid) in 20 ml of 1,2-dimethoxyethane. The dark suspension resulting from the exothermic reaction was let stand overnight. After treatment with ca. 300 ml water, the filtered aqueous solution was acidified with 6 ml of 6 N HCl. The crude product was collected, redissolved in NaHCO3 solution, and the filtered solution carefully acidified with 6 N HCl. The product was collected, washed with water, dried, and triturated with methanol to give crystals, m.p. 201°-2° dec. Recrystallization from dimethylformamide-methanol gave β-oxo-α-(2-thiazolylcarbamoyl)-β-(1-methyl-2-pyrrolyl)propionitrile, m.p. 208°-9° dec.
Workup
- additionwas added (swirling)
- customThe dark suspension resulting from the exothermic reaction
- customThe crude product was collected
- dissolutionredissolved in NaHCO3 solution
- customThe product was collected
- washwashed with water
- customdried
- customtriturated with methanol
- customto give crystals, m.p. 201°-2° dec
- customRecrystallization from dimethylformamide-methanol
Sources & evidence
- ORD record
- ord-700355ef8035426b9edb0a7a3869e187
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04435407
Linked notes
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