Hexane → N-(Diphenoxymethylene)-methanesulfonamide

HRID 2351010Notes

Reaction equation

HRID 2351010 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])C.[CH3:7][S:8]([NH2:11])(=[O:10])=[O:9].[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[CH3:7][S:8]([N:11]=[C:1]([O:4][C:5]1[CH:6]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:3][C:14]1[CH:13]=[CH:12][CH:17]=[CH:16][CH:15]=1)(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 72879Methanesulfonamide

Product 1

HCID 13738851N-(Diphenoxymethylene)-methanesulfonamideYield 49%

Procedure

267 g of diphenyl carbonate and 298 g of phosphorus pentachloride were reacted at 160° C. for 15 hours with distilling off the phosphorus oxychloride generated by the reaction. After the completion of the reaction, phosphorus oxychloride and residual phosphorus pentachloride were removed by distillation under reduced pressure to obtain dichloro-diphenoxymethane. Thereto were added 600 ml of anhydrous ethyl acetate and 148 g of methanesulfonamide, and the mixture was refluxed for 8 hours. After cooling, 1 liter of n-hexane was added to the mixture and the crystals deposited were collected by filtration. The crystals were washed with water and dried to obtain 179 g (yield: 49%) of diphenyl methanesulfonylimidocarbonate having a melting point of 124°-125.5° C.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. temperatureAfter cooling
  3. filtrationthe crystals deposited were collected by filtration
  4. washThe crystals were washed with water
  5. customdried

Sources & evidence

ORD record
ord-1f9ab6f11c464734bc710c8093a4fcff
Source dataset
uspto-grants-1989_10
Patent number
US04871765

Reaction notes

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