Water → HCID 21277739, compound

HRID 2292037Notes

Reaction equation

HRID 2292037 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[NH:14][C:15](=[O:19])[CH2:16][S:17][CH:18]=1.O>CC(C)=O>[OH:9][CH:16]1[C:15](=[O:19])[NH:14][C:13]([CH3:12])=[CH:18][S:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 21277739HCID 21277739, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

m-Chloroperbenzoic acid (0.216 g) was added to 5-methyl-2H-1,4-thiazin-3(4H)-one (0.129 g) in dry acetone (4 ml) under ice-cooling and the mixture was stirred for 2 hours. Water was added to the mixture and the solution was stirred for 30 minutes. Then, the reaction mixture was further stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel (Wakogel C-200) column, using ethyl acetate-n-hexane (=2:1) as an eluant to give 2-hydroxy-5-methyl-2H-1,4-thiazin-3(4H)-one (0.068 g, yield 46.9%) as white crystals.

Workup

  1. temperaturecooling
  2. stirringthe solution was stirred for 30 minutes
  3. stirringThen, the reaction mixture was further stirred at ambient temperature for 3 hours
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed on silica gel (Wakogel C-200) column

Sources & evidence

ORD record
ord-c4b7a67e7a69486d96da062bf8b19e25
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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