Water → (1-Methylcyclohexyl)methane sulfamate

HRID 1380663Notes

Reaction equation

HRID 1380663 reaction equation
[CH3:1][C:2]1([CH2:8]O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[S:12](Cl)(=[O:15])(=[O:14])[NH2:13].[OH2:17]>CN(C=O)C>[S:12](=[O:15])(=[O:17])([OH:14])[NH2:13].[CH3:1][C:2]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 1501840(1-Methylcyclohexyl)methanol

Product 1

HCID 67624085(1-Methylcyclohexyl)methane sulfamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold solution (-4° C.) of (1-methylcyclohexyl)methanol (6.2 g, 0.048 mol) in DMF (90 ml) was added 50% oily sodium hydride (2.81 g, 0.059 mol as NaH). After stirring for 1 hr, sulfamoyl chloride (7.82 g, 0.062 mol) was added and the stirring was continued for an additional 30 min at -4° C. The reaction mixture was poured into cold water and extracted with toluene. The organic layer was dried (Na2SO4) and the solvents were removed under vacuum to give a syrup which crystallized upon cooling. Recrystallization from chloroform/hexane gave pure (1-methylcyclohexyl)methane sulfamate, mp 40°-42° C.

Workup

  1. waitthe stirring was continued for an additional 30 min at -4° C
  2. extractionextracted with toluene
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvents were removed under vacuum
  5. customto give a syrup which
  6. customcrystallized
  7. temperatureupon cooling
  8. customRecrystallization from chloroform/hexane

Sources & evidence

ORD record
ord-711eb1dfc8de4c25ba24471bbf16414a
Source dataset
uspto-grants-1986_04
Patent number
US04582916

Reaction notes

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