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

HRID 1421958Notes

Reaction equation

HRID 1421958 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 stirred 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. stirringstirred overnight
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with ethanol and diethyl ether
  6. customdried
  7. customRecrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-d1fc850d47804cac8f1c2d736cc78aee
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

Loading…