Thioacetamide → 6-Methyl-5-(2-methyl-1,3-thiazol-4-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]#[N:14])[C:8](=[O:12])[NH:9][C:10]=1[CH3:11])=O.[C:15]([NH2:18])(=[S:17])[CH3:16]>CN(C)C=O>[CH3:11][C:10]1[NH:9][C:8](=[O:12])[C:7]([C:13]#[N:14])=[CH:6][C:5]=1[C:3]1[N:18]=[C:15]([CH3:16])[S:17][CH:2]=1Participants
Procedure
C-1. 1,2-Dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarbonitrile--A mixture containing 25.4 g of 5-(bromoacetyl)-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile, 7.5 g of thioacetamide and 100 ml of dimethylformamide was heated with stirring on a steam bath for 5 hours and then concentrated on a rotary evaporator. To the residual material was added 100 ml of water and 10 ml of concentrated aqueous ammonium hydroxide. The resulting mixture was filtered and the filtrate reacidified by adding acetic acid. The solid that separated was collected, washed with water and dried, and then recrystallized from dimethylformamide to produce 8.8 g of 1,2-dihydro-6-methyl-5-(2-methyl-4-thiazolyl)-2-oxo-3-pyridinecarbonitrile, m.p. 305°-307° C. with decomposition.
Workup
- temperaturewas heated
- concentrationconcentrated on a rotary evaporator
- additionTo the residual material was added 100 ml of water and 10 ml of concentrated aqueous ammonium hydroxide
- filtrationThe resulting mixture was filtered
- additionby adding acetic acid
- customThe solid that separated
- customwas collected
- washwashed with water
- customdried
- customrecrystallized from dimethylformamide
Sources & evidence
- ORD record
- ord-04474c9fdc6140f29dad725eac1f0ca8
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04469699
Reaction notes
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