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

HRID 1271686Notes

Reaction equation

HRID 1271686 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>[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

4

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

4H-Benzo[1,4]thiazin-3-one (7.0 g) was added cautiously portionwise to chlorosulfonic acid (15 ml) at 0° C. over 20 minutes and the solution was stirred cold for 1 hour and then heated at 45° C. for 2 hours. It was cooled and poured slowly into iced-water. The product was collected, washed well with water and dried in vacuo to give a white solid (7.0 g).

Workup

  1. temperatureIt was cooled
  2. customThe product was collected
  3. washwashed well with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3cab667f9a744be98db6a862730f6462
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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