Water → 2-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide Ethylene Ketal

HRID 964942Notes

Reaction equation

HRID 964942 reaction equation
[H-].[Na+].[CH2:3]1[O:18][C:6]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[NH:8][CH2:7]2)[O:5][CH2:4]1.Br[CH2:20][CH2:21][CH2:22][Cl:23].O>COCCOC.CCOCC>[CH2:3]1[O:18][C:6]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[N:8]([CH2:20][CH2:21][CH2:22][Cl:23])[CH2:7]2)[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 218178932H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal

Product 1

HCID 121117312-(3-Chloropropyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide Ethylene KetalYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

In 1,2-dimethoxyethane (450 mL) was suspended 60% sodium hydride (2.0 g, 502 mmol.), and then 2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal (12.06 g, 50 mmol.) was added to the suspension. The suspension was heated to 100° C. for 1 hour under stirring. The reaction liquid was cooled to 50° C., and to this was added a solution of 1-bromo-3-chloropropane (23.62 g, 150 mmol.) in 1,2-dimethoxyethane (50 mL). The mixture was heated to 100° C. for 21 hours under refluxing. The reaction liquid was filtered to remove insolubles and the solvent was evaporated to give a residue. The residue was treated with water and ether, and the organic layer was taken out. The organic solution was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated to leave the desired compound (8.89 g, yield 56%) as a yellow oil.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to 50° C.
  3. temperatureThe mixture was heated to 100° C. for 21 hours
  4. temperatureunder refluxing
  5. customThe reaction liquid
  6. filtrationwas filtered
  7. customto remove insolubles
  8. customthe solvent was evaporated
  9. customto give a residue
  10. washThe organic solution was washed with water
  11. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  12. customThe solvent was evaporated

Sources & evidence

ORD record
ord-67b7895bd6bf40f39c5f6343b0b3de84
Source dataset
uspto-grants-1998_06
Patent number
US05773437

Reaction notes

Loading…