Chlorosulfamic acid → HCID 76836077, compound

HRID 660419Notes

Reaction equation

HRID 660419 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]2[O:6][C@@H:7]([CH2:10][OH:11])[CH2:8][O:9][C:4]=2[CH:3]=1.[H-].[Na+].[S:17](Cl)(=[O:20])(=[O:19])[NH2:18]>CN(C=O)C.O>[S:17](=[O:20])(=[O:19])([O:11][CH2:10][CH:7]1[O:6][C:5]2[CH:12]=[C:13]([Cl:14])[C:2]([Cl:1])=[CH:3][C:4]=2[O:9][CH2:8]1)[NH2:18]

Participants

6

Reactant 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 66687022(2s)-6,7 Dichloro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethanol

Product 1

HCID 76836077HCID 76836077, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2S)-6,7 dichloro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethanol (2.0 g, 8.5 mmol), prepared according to the procedure described in Example 11 above, in DMF (20 mL) was cooled in an ice bath. Then, 95% sodium hydride (0.28 g, 11 mmol) was added under argon and the reaction mixture was stirred 30 min. Sulfamoyl chloride (1.97 g, 17 mmol) was added and the reaction mixture was stirred with ice bath cooling. After 1 h, the reaction mixture was diluted with water (50 mL) and extracted three times with ethyl acetate. The combined ethyl acetate was washed with brine, dried (Na2SO4) and evaporated in vacuo to an oil, which was purified by flash column chromatography (ethyl acetate/heptane 1:1) to yield a white solid. The white solid was recrystallized from benzene to yield the title compound as a white solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringthe reaction mixture was stirred with ice bath
  3. temperaturecooling
  4. waitAfter 1 h
  5. extractionextracted three times with ethyl acetate
  6. washThe combined ethyl acetate was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo to an oil, which
  9. customwas purified by flash column chromatography (ethyl acetate/heptane 1:1)
  10. customto yield a white solid
  11. customThe white solid was recrystallized from benzene

Sources & evidence

ORD record
ord-f518a0cbcf63456fb1de0705484e845a
Source dataset
uspto-grants-2011_12
Patent number
US08084490B2

Reaction notes

Loading…