m-Chloroperbenzoic acid → 3-(3,5-Dichloro-4-methoxybenzoyl)-1-oxo-2,3-dihydro-1,3-benzothiazole

HRID 385008Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:21])[C:18]=1[O:19][CH3:20])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8]1)=[O:6].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:21])[C:18]=1[O:19][CH3:20])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:30])[CH2:8]1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(3,5-dichloro-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole (500 mg) was dissolved in chloroform (10 mL), and 70% metachloroperbenzoic acid (320 mg) was added to the solution, and the mixture was stirred at 0° C. for 10 minutes. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N sodium hydroxide 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 (336 mg) as a colorless crystal.

Workup

distillationThe solvent was distilled off under reduced pressure and water
additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with 1N sodium hydroxide 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-2e437cf7552243edb82282d402d56e02
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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