Hydrochloric Acid → 2-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-Dioxide

HRID 964949Notes

Reaction equation

HRID 964949 reaction equation
C1O[C:4]2([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[S:7](=[O:15])(=[O:14])[N:6]([CH2:16][CH2:17][CH2:18][Cl:19])[CH2:5]2)[O:3]C1.Cl>CO>[Cl:19][CH2:18][CH2:17][CH2:16][N:6]1[CH2:5][C:4](=[O:3])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7]1(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 121117312-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide Ethylene Ketal

Product 1

HCID 187599102-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-DioxideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(3-chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal (5.0 g, 15.7 mmol.), 3N aqueous hydrochloric acid (30 mL) and methanol (30 mL) was heated under refluxing for 20 min. Methanol was distilled off under reduced pressure. To the residue was added water (30 mL), and the mixture was extracted with ethyl ether. The ethyl ether portion was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill the solvent off, to give the desired compound (4.19 g, 100%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 20 min
  3. distillationMethanol was distilled off under reduced pressure
  4. additionTo the residue was added water (30 mL)
  5. extractionthe mixture was extracted with ethyl ether
  6. washThe ethyl ether portion was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationto distill the solvent off,

Sources & evidence

ORD record
ord-3e4168aafcfa4e9dbf0e366ed05a5c5b
Source dataset
uspto-grants-1998_06
Patent number
US05773437

Reaction notes

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