4H-1,4-Benzothiazin-3-one → 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonyl chloride

HRID 1767039Notes

Reaction equation

HRID 1767039 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[O:11]=[C:3]1[NH:4][C:5]2[CH:10]=[C:9]([S:13]([Cl:12])(=[O:15])=[O:14])[CH:8]=[CH:7][C:6]=2[S:1][CH2:2]1

Participants

3

Reactant 2

HCID 213964H-1,4-Benzothiazin-3-oneHCID 24638Chlorosulfonic acid

Product 1

HCID 218737563-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonyl chloride

Procedure

Powdered 4H benzo[1,4]thiazin-3-one (7.0g) was added cautiously, portionwise (over 20 minutes), to chlorosulfonic acid (15 mL), cooled in ice. After 1 hour, the blue solution was allowed to warm to room temperature and it was heated at 45° C. for 2 hours, cooled and poured into ice. The solid was collected, washed with water, and hexane, and dried in vacuo, to give a white solid (7.0 g): LC-MS (ES) m/e 263 (M)+.

Workup

  1. additionwas added cautiously
  2. temperatureit was heated at 45° C. for 2 hours
  3. temperaturecooled
  4. additionpoured into ice
  5. customThe solid was collected
  6. washwashed with water, and hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-eef4f69d7adc4896801bb9fb38cd00a5
Source dataset
uspto-grants-2007_06
Patent number
US07232832B2

Reaction notes

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