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

HRID 385019Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

3-(3-cyano-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole (232 mg) was dissolved in N,N-dimethylformamide (3 mL), and lithium chloride (108 mg) was added to the solution, and then the mixture was stirred at 70° C. for 1 hour. To the reaction solution, 1N hydrochloric acid was added, and then the 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 and the obtained residue was crystallized from n-hexane-ethyl acetate to obtain the title compound (131 mg) as a brown crystal.

Workup

extractionthe 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
customthe obtained residue was crystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-12c30ea19c0742bdb2b2bb5d5ff47366
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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