N-(Diphenoxymethylene)-methanesulfonamide → N-methanesulfonyl-N'-[2-[[5-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)aminomethyl]-2furyl]methylthio]ethyl]-O-phenylisourea

HRID 2351014Notes

Reaction equation

HRID 2351014 reaction equation
[CH3:1][S:2]([N:5]=[C:6]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)OC1C=CC=CC=1)(=[O:4])=[O:3].[CH3:21][N:22]([CH2:31][C:32]1[O:36][C:35]([CH2:37][S:38][CH2:39][CH2:40][NH2:41])=[CH:34][CH:33]=1)[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24]>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6](=[N:41][CH2:40][CH2:39][S:38][CH2:37][C:35]1[O:36][C:32]([CH2:31][N:22]([CH3:21])[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24])=[CH:33][CH:34]=1)[O:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 13738851N-(Diphenoxymethylene)-methanesulfonamideHCID 146717492-[[5-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)aminomethyl]-2furyl]methylthio]ethylamine

Product 1

HCID 19847901N-methanesulfonyl-N'-[2-[[5-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)aminomethyl]-2furyl]methylthio]ethyl]-O-phenylisoureaYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.6 g of diphenyl methanesulfonylimidocarbonate was dissolved in 40 ml of methylene chloride. With ice-cooling, thereto was added 15 g of 2-[[5-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)aminomethyl]-2furyl]methylthio]ethylamine. The mixture was stirred for 10 minutes. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: benzene:ethyl acetate=2:1) to obtain 17.8 g (yield: 78%) of oily N-methanesulfonyl-N'-[2-[[5-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)aminomethyl]-2furyl]methylthio]ethyl]-O-phenylisourea.

Workup

  1. temperatureWith ice-cooling
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by a column chromatography (eluant: benzene:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e0e9d4ffb1b143bd82890815b91456a9
Source dataset
uspto-grants-1989_10
Patent number
US04871765

Reaction notes

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