Hydrochloric Acid → HCID 51349183, compound

HRID 385044Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([CH:24]([CH3:26])[CH3:25])[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]([CH:24]([CH3:26])[CH3:25])[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:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

3-(3-cyano-5-isopropyl-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (434 mg) was dissolved in N,N-dimethylformamide (5 mL), and lithium chloride (496 mg) was added to the solution, and then the mixture was stirred at 100° C. for 20 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-chloroform to obtain the title compound (351 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
customthe obtained residue was crystallized from n-hexane-chloroform

Sources & evidence

ORD record: ord-b658520358694ecdafb79b5c8c9a4435
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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