Hydrochloric Acid → HCID 51349327, compound

HRID 385160Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

3-(3-cyano-4-methoxy-5-trifluoromethylbenzoyl)-1,1-dioxo-5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole (459 mg) was dissolved in N,N-dimethylformamide (4.5 mL), and lithium chloride (169 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-chloroform to obtain the title compound (411 mg) as a colorless 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-chloroform

Sources & evidence

ORD record: ord-f377f8b87aad492b903d6f0d7912415b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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