Water → HCID 11552354, compound
Reaction equation
ClC(Cl)(Cl)COC([N:7]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:8]([O:10]CC(Cl)(Cl)Cl)=O)=O.[C:24]1([C:30]2[N:34]=[C:33]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[S:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:24]1([C:30]2[N:34]=[C:33]([N:35]3[CH2:40][CH2:39][N:38]([C:8]([NH:7][C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[O:10])[CH2:37][CH2:36]3)[S:32][N:31]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixed solution of bis(2,2,2-trichloroethyl)pyridin-3-ylimidodicarbonate (271 mg, 0.610 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.211 ml, 1.22 mmol) in dimethyl sulfoxide (2 ml) was stirred at 70° C. for 3 hours and further stirred at 80° C. for 1 hour. Water was poured to the reaction mixture, and the resulting solution 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 purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and ethyl acetate to give 106 mg (47.5%) of the desired product as a solid.
Workup
- extractionthe resulting solution 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 purified by silica gel column chromatography (ethyl acetate)
- customrecrystallized from a mixed solvent of hexane and ethyl acetate
Sources & evidence
- ORD record
- ord-967e585a5397499fac8df6e988a5d0d8
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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