Hydrochloric Acid → HCID 68109266, compound

HRID 385018Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[C:21]=1[O:22]C)[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[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:19]=[C:20]([C:24]([F:27])([F:25])[F:26])[C:21]=1[OH:22])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:17])(=[O:18])[CH2:9]1)=[O:7])#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

3-(3-cyano-4-methoxy-5-trifluoromethylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (4.08 g) was dissolved in N,N-dimethylformamide (40 mL), and lithium chloride (1.74 g) was added to the solution, and then the mixture was stirred at 70° C. for 2 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 and the obtained residue was crystallized from n-hexane-ethyl acetate to obtain the title compound (222 g) 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
customthe obtained residue was crystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-f892918d73224b75a22379508ed53828
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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