Water → HCID 68779922, compound

HRID 2263145Notes

Reaction equation

[CH3:1][C:2]1[N:6]=[C:5]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[S:4][N:3]=1.[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH3:1][C:2]1[N:6]=[C:5]([NH:7][C:8]([N:30]2[CH2:31][CH2:32][N:27]([C:25]3[S:24][N:23]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:26]=3)[CH2:28][CH2:29]2)=[O:15])[S:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trichloroethyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate (260 mg, 0.893 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.156 ml, 0.893 mmol) in dimethylsulfoxide (2.7 ml) was stirred at 70° C. for 15 hours. Water was poured into 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 purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and ethyl acetate to obtain the desired product (116 mg, 36.8%) 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 purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record: ord-fe8d8a8a2bd54e76ad20f5e40c754f61
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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