m-Chloroperbenzoic acid → HCID 15027625, compound

HRID 1090642Notes

Reaction equation

HRID 1090642 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([C:18]2[C:19](=[O:32])[N:20]([CH2:29][CH2:30][CH3:31])[C:21](=[O:28])[N:22]3[CH2:27][CH:26]=[CH:25][S:24][C:23]=23)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[O:9]=[S:24]1[CH2:25][CH:26]=[CH:27][N:22]2[C:21](=[O:28])[N:20]([CH2:29][CH2:30][CH3:31])[C:19](=[O:32])[C:18]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:23]12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9972023HCID 9972023, compound

Product 1

HCID 15027625HCID 15027625, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (0.34 g)was added to a solution of 9-phenyl-7-propyl-4H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (0.53 g) in methylene chloride (10 mll) little by little with stirring under ice cooling, and then, the reaction mixture was stirred at room temperature for 10 hours. An insoluble material was removed by filtration, and the filtrate was washed with a saturated aqueous sodium bicarbonate. After drying, the organic solution was concentrated to dryness. The resulting residue was purified column chromatography on silica gel. The resulting crude crystals were recrystalized from methylene chloride-isopropyl ether to give colorless needles (0.47 g, 87%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 10 hours
  2. customAn insoluble material was removed by filtration
  3. washthe filtrate was washed with a saturated aqueous sodium bicarbonate
  4. customAfter drying
  5. concentrationthe organic solution was concentrated to dryness
  6. customThe resulting residue was purified column chromatography on silica gel
  7. customThe resulting crude crystals were recrystalized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-45875a8ab05f4b9392097fa43bfee385
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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