Hydrochloric Acid → HCID 68109415, compound

HRID 385129Notes

Reaction equation

C[O:2][C:3]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:6]([C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11](=[O:19])(=[O:18])[CH2:10]2)=[O:8])=[CH:5][C:4]=1[C:26]([N:28]1[CH2:32][CH2:31][S:30][CH2:29]1)=[O:27].[Cl-].[Li+].Cl>CN(C)C=O>[OH:2][C:3]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:6]([C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11](=[O:19])(=[O:18])[CH2:10]2)=[O:8])=[CH:5][C:4]=1[C:26]([N:28]1[CH2:32][CH2:31][S:30][CH2:29]1)=[O:27]

Participants

Conditions

Temperature: 120 °C

Procedure

3-[4-methoxy-3-(1,3-thiazolidine-3-carbonyl)-5-trifluoromethylbenzoyl]-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (138 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (118 mg) was added to the solution, and then the mixture was stirred at 120° C. for 1.5 hours. To the reaction solution, 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was crystallized from n-hexane-chloroform to obtain the title compound (47 mg) as a pale yellow crystal.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe obtained residue was crystallized from n-hexane-chloroform

Sources & evidence

ORD record: ord-267ca1542bb641b49da7fea3bb354948
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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