m-Chloroperbenzoic acid → 2-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one

HRID 2292030Notes

Reaction equation

HRID 2292030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1.[CH3:12][C:13]1[NH:14][C:15](=[O:25])[CH2:16][S:17][C:18]=1[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8]([O:10][CH:16]1[C:15](=[O:25])[NH:14][C:13]([CH3:12])=[C:18]([C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)[S:17]1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 30625322H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-

Product 1

HCID 139360302-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-oneYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (8.97 g, 70% purity) was added to a solution of 5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (5.0 g) in dichloromethane (120 ml) under ice/water-cooling and the mixture was stirred for 10 minutes under ice/water-cooling. The mixture was washed with saturated sodium bicarbonate aqueous solution (2 times) and successively with water (1 time) and was dried over magnsium sulfate. The solvent was removed under reduced pressure and the residue was recrystallized from ether-petrolem ether to give the titled compound (3.29 g, yield 37.6%) as pale yellow needles.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washThe mixture was washed with saturated sodium bicarbonate aqueous solution (2 times) and successively with water (1 time)
  4. dry with materialwas dried over magnsium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was recrystallized from ether-petrolem ether

Sources & evidence

ORD record
ord-d72e1f4673334960b9298eb2c670d763
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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