Sulfamide → Diphenyl sulfamoylcarbonimidate

HRID 1892140Notes

Reaction equation

HRID 1892140 reaction equation
Cl[C:2](Cl)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[S:18]([NH2:22])([NH2:21])(=[O:20])=[O:19]>CC#N>[S:18]([N:22]=[C:2]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:20])(=[O:19])[NH2:21]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 5116898Dichlorodiphenoxymethane

Product 1

HCID 15599173Diphenyl sulfamoylcarbonimidateYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dichlorodiphenoxymethane (1 g, 3.72 mmol) and sulfamide (0.72 g, 7.44 mmol) were dissolved in MeCN (10 ml) and stirred at room temperature for 18 hours. The mixture was concentrated under vacuum and purified by flash chromatography (20-40% EtOAc/hexanes) to afford diphenyl sulfamoylcarbonimidate (0.69 g, 2.34 mmol, 63%) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by flash chromatography (20-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2991f00cb6864d5aaa46bfba5aae8fdf
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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