Water → 2-(N-isobutyryl-N-methylamino)-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole
Reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][C:9](=[O:21])[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]=1.[C:22](Cl)(=[O:26])[CH:23]([CH3:25])[CH3:24].O>N1C=CC=CC=1>[C:22]([N:2]([C:3]1[S:4][CH:5]=[C:6]([CH2:8][C:9](=[O:21])[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]=1)[CH3:1])(=[O:26])[CH:23]([CH3:25])[CH3:24]Participants
5
Procedure
A solution containing 7.6 g (0.025 mole) of 2-methylamino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole and 2.9 g (0.027 mole) of isobutyryl chloride in 25 ml of pyridine was heated at about 45° for 24 hours. The mixture was poured into water. The thick oil failed to crystallize. The aqueous phase was decanted and the residue was dissolved in benzene. The organic phase was washed with water, dried over sodium sulfate and cooled. With stirring, hexane was added and a crystalline product precipitated. There was obtained 5.8 g of the desired amide, m.p. 122°-23°. N.M.R. (dimethyl-d6 sulfoxide) ∂ 1.1-1.3 (2×CH3), 2.7-3.4 (CH, septet), 3.6 (NCH3), 3.7 (CH2), 6.9 (hetero-aromatic), 7.3-8.1 (aromatic), 10.4 (HNC=0).
Workup
- temperaturewas heated at about 45° for 24 hours
- customto crystallize
- customThe aqueous phase was decanted
- dissolutionthe residue was dissolved in benzene
- washThe organic phase was washed with water
- dry with materialdried over sodium sulfate
- temperaturecooled
- additionhexane was added
- customa crystalline product precipitated
Sources & evidence
- ORD record
- ord-08ed975b7d2942a6b4c533e751db8bae
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04152329
Reaction notes
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