Dimethyl Sulfoxide → HCID 68779567, compound

HRID 2262915Notes

Reaction equation

[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:44]=[CH:43][C:22]2[C:23]([N:26](C(OCC(Cl)(Cl)Cl)=O)[C:27](OCC(Cl)(Cl)Cl)=[O:28])=[N:24][O:25][C:21]=2[CH:20]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[F:18][C:19]1[CH:44]=[CH:43][C:22]2[C:23]([NH:26][C:27]([N:15]3[CH2:16][CH2:17][N:12]([C:10]4[S:9][N:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:11]=4)[CH2:13][CH2:14]3)=[O:28])=[N:24][O:25][C:21]=2[CH:20]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (492 mg, 2.00 mmol), bis(2,2,2-trichloroethyl) (6-fluoro-1,2-benzisoxazol-3-yl)imidodicarbonate (502 mg, 1.00 mmol), diisopropylethylamine (0.174 ml, 1.00 mmol) and dimethyl sulfoxide (5 ml) was stirred at 70° C. for 5 hours. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to yield 136 mg (32.1%) of the desired product.

Workup

extractionextracted 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 tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record: ord-b707496ce6744e08902dbc5dba50552c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

Loading…