4H-1,4-Benzothiazin-3-one → 2H-1,4-Benzothiazin-3(4H)-one 1-oxide

HRID 1825755Notes

Reaction equation

HRID 1825755 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[S:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14](=[O:22])[CH2:13]1>ClCCl>[O:9]=[S:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14](=[O:22])[CH2:13]1

Participants

4

Reactant 2

HCID 213964H-1,4-Benzothiazin-3-oneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 3698042H-1,4-Benzothiazin-3(4H)-one 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (1.35 g, 6.6 mmol) in dry dichloromethane (40 ml) was added dropwise to an ice cooled solution of 2H-1,4-benzothiazin-3(4H)-one (1.10 g, 6.6 mmol) in dry dichloromethane (100 ml) with stirring. The reaction mixture was allowed to reach room temperature, then stirred overnight. The product was collected by filtration and washed with dichloromethane. Yield 0.54 g (45%) mp 184–6° C.

Workup

  1. customto reach room temperature
  2. stirringstirred overnight
  3. filtrationThe product was collected by filtration
  4. washwashed with dichloromethane

Sources & evidence

ORD record
ord-4ea1da8f9ed944d0a0c582bb0c05cdbd
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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