m-Chloroperbenzoic acid → 2-(3-Methoxy-4-methylsulfonylphenyl)-4-(3,4-dihydrocarbostyril-6-yl)thiazole

HRID 1699553Notes

Reaction equation

HRID 1699553 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)[N:16]=2)[CH:6]=[CH:7][C:8]=1[S:9]([CH3:11])=[O:10].ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)[N:16]=2)[CH:6]=[CH:7][C:8]=1[S:9]([CH3:11])(=[O:36])=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 117415922-(3-Methoxy-4-methylsulfinylphenyl)-4-(3,4-dihydrocarbostyril-6-yl)thiazole

Product 1

HCID 103417332-(3-Methoxy-4-methylsulfonylphenyl)-4-(3,4-dihydrocarbostyril-6-yl)thiazoleYield 16.6%

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

In 100 ml of chloroform-ethanol was suspended 2.9 g of 2-(3-methoxy-4-methylsulfinylphenyl)- 4- (3,4-dihydrocarbostyril-6-yl)thiazole. Under ice-cooling, 1.72 g of m-chloroperbenzoic acid (80%) was added in small portions and the mixture was stiffed for 1 hour. Then, the mixture was returned to room temperature and stirred overnight. The resulting crystals were collected by filtration, washed with ethanol and diethyl ether, and dried. Recrystallization from dimethylformamide-water to obtain 0.50 g of 2-(3-methoxy-4-methylsulfonylphenyl)-4-(3,4- dihydrocarbostyril-6-yl)thiazole as a white powder.

Workup

  1. temperatureUnder ice-cooling
  2. customwas returned to room temperature
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with ethanol and diethyl ether
  5. customdried
  6. customRecrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-a9d7d24ea8054c8baffd4999073dc2eb
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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