Hydrochloric Acid → HCID 86668172, compound

HRID 385105Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[C:23]=1[O:24]C)[C:8]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:20])(=[O:19])[CH2:11]1)=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].Cl>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[C:23]=1[OH:24])[C:8]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:20])(=[O:19])[CH2:11]1)=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 130 °C

Procedure

3-(3-t-butyl-4-methoxy-5-methylsulfonylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (232 mg) was dissolved in N,N-dimethylformamide (5 mL), and lithium chloride (225 mg) was added to the solution, and then the mixture was stirred at 130° C. for 2 hours. To the reaction solution, 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, 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 purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (201 mg) as a colorless amorphous product.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water, 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 purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-792a560f7a3c43afadd761d728b4f7c6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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