Chlorosulfamic acid → 60548-64-3

HRID 616731Notes

Reaction equation

HRID 616731 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH3:9])([CH2:5][OH:6])[CH2:3][OH:4].[H-].[Na+].[S:12](Cl)(=[O:15])(=[O:14])[NH2:13]>C(COC)OC>[CH3:1][C:2]([CH2:7][CH2:8][CH3:9])([CH2:5][O:6][S:12](=[O:15])(=[O:14])[NH2:13])[CH2:3][O:4][S:12](=[O:15])(=[O:14])[NH2:13]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 662202-Methyl-2-propylpropane-1,3-diol

Product 1

HCID 1270892560548-64-3

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
4 °C

Procedure

To a solution of 10 g. (0.076 mol.) of 2-methyl-2-propyl-1,3-propanediol in 200 ml. of dimethoxyethane is added 12.7 g. (0.3 mol.) of 57% sodium hydride followed by an additional 400 ml. of dimethoxyethane. After stirring overnight the suspension is cooled to 4° C and a solution of 31.2 g. (0.27 mol.) of sulfamoyl chloride in 600 ml. of dimethoxyethane is added dropwise. The resulting suspension is stirred overnight at room temperature. The mixture is then filtered, the filtrate is concentrated and the residue washed with heptane. The residue is then chromatographed through SilicAR, CC-7 and eluted with 25% acetone-chloroform. The solid obtained after removel of the solvent is crystallized from a mixture of ethyl acetate-hexane-methylene chloride to afford 2-methyl-2-propyl-1,3-bis-O-sulfamyl-1,3-propanediol, m.p. 92°-94° C.

Workup

  1. stirringThe resulting suspension is stirred overnight at room temperature
  2. filtrationThe mixture is then filtered
  3. concentrationthe filtrate is concentrated
  4. washthe residue washed with heptane
  5. customThe residue is then chromatographed through SilicAR, CC-7
  6. washeluted with 25% acetone-chloroform
  7. customThe solid obtained after removel of the solvent
  8. customis crystallized from a mixture of ethyl acetate-hexane-methylene chloride

Sources & evidence

ORD record
ord-cea2c23ec2ab4937893ebd86f8521c40
Source dataset
uspto-grants-1978_02
Patent number
US04075351

Reaction notes

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