Water → 4-(4-Phenyl-1,3-thiazol-2-yl)-N-1,2,3-thiadiazol-5-ylpiperazine-1-carboxamide
Reaction equation
[S:1]1[C:5]([NH:6][C:7](=[O:14])OCC(Cl)(Cl)Cl)=[CH:4][N:3]=[N:2]1.[C:15]1([C:21]2[N:22]=[C:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[S:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:15]1([C:21]2[N:22]=[C:23]([N:26]3[CH2:31][CH2:30][N:29]([C:7]([NH:6][C:5]4[S:1][N:2]=[N:3][CH:4]=4)=[O:14])[CH2:28][CH2:27]3)[S:24][CH:25]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 2,2,2-trichloroethyl 1,2,3-thiadiazol-5-ylcarbamate (190 mg, 0.686 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (153 mg, 0.624 mmol) and diisopropylethylamine (0.217 ml, 1.25 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 days. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 159 mg (68.4%) of the desired product as a solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran
Sources & evidence
- ORD record
- ord-3b3a5f746c2d4e37a1e9ea3c9caedd91
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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