4-Pyridinecarbothioamide → 4-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]pyridine
Reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12]([C:14]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][N:15]=1)=O>CN1CCCC1=O>[C:19]1([CH:17]2[O:16][N:15]=[C:14]([C:12]3[N:9]=[C:1]([C:2]4[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=4)[S:8][CH:11]=3)[CH2:18]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
To a solution of thioisonicotinamide (0.5 g, 3.6 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was added 2-chloro-1-(4,5-dihydro-5-phenyl-3-isoxazolyl)ethanone (0.807 g, 3.6 mmol), at room temperature. The reaction mixture was then heated to 100° C. for 3 h. Then the reaction mixture was cooled to room temperature, quenched with water (100 mL), extracted with ethyl acetate (50 mL×2). The reaction mixture was diluted with water (50 mL) and brine (50 mL), and the organic layer was concentrated under reduced pressure and purified by medium-pressure liquid chromatography using 2% of methanol in chloroform as eluant to give 0.7 g of the title compound as a brown solid.
Workup
- customat room temperature
- temperatureThen the reaction mixture was cooled to room temperature
- customquenched with water (100 mL)
- extractionextracted with ethyl acetate (50 mL×2)
- additionThe reaction mixture was diluted with water (50 mL) and brine (50 mL)
- concentrationthe organic layer was concentrated under reduced pressure
- custompurified by medium-pressure liquid chromatography
Sources & evidence
- ORD record
- ord-87768792f5ee4b37b4d3b384c577dc25
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642634B2
Reaction notes
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