Sulfamide → Diphenyl sulfamoylcarbonimidate

HRID 1972296Notes

Reaction equation

HRID 1972296 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].Cl[C:7](Cl)([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[S:1]([N:5]=[C:7]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:3])(=[O:2])[NH2:4]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 5116898Dichlorodiphenoxymethane

Product 1

HCID 15599173Diphenyl sulfamoylcarbonimidateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of sulfamide (100.9 mg, 1.05 mmol) in anhydrous acetonitrile (3.3 mL) is slowly added dichlorodiphenoxymethane (269.1 mg, 1.00 mmol) at 0° C. The reaction mixture is stirred at room temperature overnight before removal of the solvent. The residue is purified by chromatography to provide diphenyl sulfamoylcarbonimidate (280.2 mg, 96% yield) as a white solid product; HPLC-MS calculated for C13H12N2O4S (M+H+) 293.1, found 293.1.

Workup

  1. customat 0° C
  2. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-81754bcca04045c18c30a56c3ec548ff
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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