Hydrochloric Acid → 3-(3-Cyano-4-hydroxy-5-trifluoromethylbenzoyl)-1-oxo-2,3-dihydro-1,3-benzothiazole

HRID 385021Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

3-(3-cyano-4-methoxy-5-trifluoromethylbenzoyl)-1-oxo-2,3-dihydro-1,3-benzothiazole (619 mg) was dissolved in N,N-dimethylformamide (5 mL), and lithium chloride (276 mg) was added to the solution, and the mixture was stirred at 70° C. for 3 hours. To the reaction solution, 1N hydrochloric acid was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (494 mg) as a colorless crystal.

Workup

extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with 1N hydrochloric acid and saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-1cf483024ba9486b90a203d84a081df2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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