3-Chloro-2-butanone → 4,5-Dimethyl-2-(4-trifluoromethyl-phenyl)-thiazole hydrochloride
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.[Cl:14][CH:15]([CH3:19])[C:16](=O)[CH3:17]>C(O)(C)C>[ClH:14].[CH3:19][C:15]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:4][CH:5]=2)[S:8][C:16]=1[CH3:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 4-trifluoromethyl-thiobenzamide (4 g, 19.5 mmol) and 3-chloro-2-butanone (3.9 ml, 39 mmol) in isopropanol (20 ml) was heated to reflux for 30 h under an argon atmosphere. The reaction mixture was concentrated to a volume of 10 ml, cooled to 50° C. and diisopropylether (20 ml) was added dropwise. The solution was cooled to ambient temperature, the resulting crystals were filtered off, washed with ice cold diisopropylether and dried in vacuo to give 2.6 g (8.9 mmol, 45%) of the title compound as off-white crystals.
Workup
- temperatureto reflux for 30 h under an argon atmosphere
- concentrationThe reaction mixture was concentrated to a volume of 10 ml
- additiondiisopropylether (20 ml) was added dropwise
- temperatureThe solution was cooled to ambient temperature
- filtrationthe resulting crystals were filtered off
- washwashed with ice cold diisopropylether
- customdried in vacuo
Sources & evidence
- ORD record
- ord-a32c5eb6a9cc40ad8d7fa7ad8f444e29
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07235572B2
Reaction notes
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