Hydrochloric Acid → Hepsulfam

HRID 1761901Notes

Reaction equation

HRID 1761901 reaction equation
[H-].[Na+].[CH2:3]([OH:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[S:12](Cl)(=[O:15])(=[O:14])[NH2:13].Cl>O1CCCC1.O>[S:12]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:11][S:12](=[O:15])(=[O:14])[NH2:13])(=[O:15])(=[O:14])[NH2:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 123811,7-HeptanediolHCID 24499Chlorosulfamic acidHCID 24758Sodium hydride

Product 1

HCID 100606HepsulfamYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent5×

Procedure

A 57% oil dispersion of sodium hydride (11.8 g, 0.28 mole NaH) was added to 150 ml of tetrahydrofuran. The suspension was stirred and gently heated, and 15.84 g (0.12 mole) of 1,7-heptanediol in 75 ml of tetrahydrofuran was added gradually over a period of 90 minutes. An additional 25 ml of tetrahydrofuran was then added, and the reaction mixture was stirred at reflux for five hours. An additional 150 ml of tetrahydrofuran was added, and to the stirred warm mixture there was added dropwise a solution of 28.9 g (0.25 mole) of sulfamoyl chloride in 150 ml of tetrahydrofuran over a two hour period. The reaction mixture was stirred at reflux for five hours, then cooled and treaated dropwise with 125 ml of water. The mixture was acidified with 2N hydrochloric acid, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue triturated with ethyl acetate to give a yellow solid which was recrystallized from an ethyl acetate--hexane mixture to give 22.0 g of 1,7-heptanediol disulfamate as colorless granules, m.p. 87°-88° C.

Workup

  1. temperaturegently heated
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux for five hours
  4. temperatureto the stirred warm mixture there
  5. stirringThe reaction mixture was stirred
  6. temperatureat reflux for five hours
  7. temperaturecooled
  8. customthe organic layer was separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed in vacuo
  11. customthe residue triturated with ethyl acetate
  12. customto give a yellow solid which
  13. customwas recrystallized from an ethyl acetate

Sources & evidence

ORD record
ord-79e471cba6984de885a9657bf1eb3d6d
Source dataset
uspto-grants-1989_05
Patent number
US04829084

Reaction notes

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