m-Chloroperbenzoic acid → 3-(3-Cyano-4-methoxy-5-trifluoromethylbenzoyl)-1-oxo-2,3-dihydro-1,3-benzothiazole

HRID 385020Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:19]=1[O:20][CH3:21])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][CH2:9]1)=[O:7])#[N:2].ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:19]=1[O:20][CH3:21])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:34])[CH2:9]1)=[O:7])#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(3-cyano-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole (594 mg) was dissolved in chloroform (10 mL), and 70% metachloroperbenzoic acid (433 mg) was added to the solution, and then the mixture was stirred at 0° C. for 5 minutes. The organic solvent was distilled off under reduced pressure, and then 1N sodium hydroxide was added and the precipitated crystal was washed with 1N sodium hydroxide and water to obtain the title compound (619 mg) as a colorless crystal.

Workup

distillationThe organic solvent was distilled off under reduced pressure
addition1N sodium hydroxide was added
washthe precipitated crystal was washed with 1N sodium hydroxide and water

Sources & evidence

ORD record: ord-8515f09e0ccd40ac8f91ee5445e6573b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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