Hydrochloric Acid → 3-(3,5-Dichloro-4-hydroxybenzoyl)-1-oxo-2,3-dihydro-1,3-benzothiazole

HRID 385009Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

3-(3,5-dichloro-4-methoxybenzoyl)-1-oxo-2,3-dihydro-1,3-benzothiazole (336 mg) was dissolved in N,N-dimethylformamide (6 mL) and lithium chloride (400 mg) was added to the solution, and then the mixture was stirred at 120° C. for 16 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 ethyl acetate-methanol to obtain the title compound (220 mg) as a brown 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 ethyl acetate-methanol

Sources & evidence

ORD record: ord-35c30e470233476f9d37fbd68f9aaa0f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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