Methanesulfonamide → N-(Diphenoxymethylene)-methanesulfonamide

HRID 1892137Notes

Reaction equation

HRID 1892137 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.[CH3:18][S:19]([NH2:22])(=[O:21])=[O:20]>CCOC(C)=O>[CH3:18][S:19]([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:21])=[O:20]

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 5116898Dichlorodiphenoxymethane

Product 1

HCID 13738851N-(Diphenoxymethylene)-methanesulfonamideYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dichlorodiphenoxymethane (2 g, 7.46 mmol) and methylsulfonamide (1.56 g, 16.41 mmol) were dissolved in EtOAc (15 ml) and heated to reflux for 12 hours. The mixture was allowed to cool and was concentrated under vacuum. Purification of the crude mixture by flash chromatography (20% EtOAc/hexanes) afforded diphenyl methylsulfonylcarbonimidate (0.75 g, 2.59 mmol, 35%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. temperatureto cool
  4. concentrationwas concentrated under vacuum
  5. customPurification of the crude mixture by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ba0a139c0cc145c4b92af88b1ebbac74
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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