Chlorosulfamic acid → 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol

HRID 1973472Notes

Reaction equation

HRID 1973472 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:10][OH:11])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[S:20](Cl)(=[O:23])(=[O:22])[NH2:21]>C(COC)OC>[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:8][O:9][S:20](=[O:23])(=[O:22])[NH2:21])[CH2:10][O:11][S:20](=[O:23])(=[O:22])[NH2:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 4104452,2-Diphenylpropane-1,3-diol

Product 1

HCID 203689762,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
4 °C

Procedure

To a solution of 17.3 g. (0.076 mol.) of 2,2-diphenyl-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. A solution of 31.2 g. (0.27 mol.) of sulfamoyl chloride in 600 ml. of dimethoxyethane is then added dropwise. The suspension is stirred overnight at room temperature. After filtering the mixture the filtrate is concentrated and the residue washed with heptane. Chromatography on SilicAR, CC-7, followed by crystallization affords 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol.

Workup

  1. stirringThe suspension is stirred overnight at room temperature
  2. filtrationAfter filtering the mixture the filtrate
  3. concentrationis concentrated
  4. washthe residue washed with heptane
  5. customChromatography on SilicAR, CC-7, followed by crystallization

Sources & evidence

ORD record
ord-230138b3642e4da3b310957da7f385ae
Source dataset
uspto-grants-1976_12
Patent number
US03997585

Reaction notes

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