phenyl N-[(N-dimethylsulfamoyl-N-methylamino)sulfonyl]carbamate → 1-[(N-dimethylsulfamoyl-N-methylamino)sulfonylcarbamoyl]-3-methyl-5-(2-thienyl)-2-pyrazoline

HRID 465280Notes

Reaction equation

HRID 465280 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([N:6]([S:8]([NH:11][C:12](=[O:20])OC1C=CC=CC=1)(=[O:10])=[O:9])[CH3:7])(=[O:5])=[O:4].[CH3:22][C:23]1[CH2:27][CH:26]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[NH:25][N:24]=1>C1C=CC=CC=1>[CH3:21][N:2]([CH3:1])[S:3]([N:6]([S:8]([NH:11][C:12]([N:25]1[CH:26]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C:23]([CH3:22])=[N:24]1)=[O:20])(=[O:9])=[O:10])[CH3:7])(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 19873528phenyl N-[(N-dimethylsulfamoyl-N-methylamino)sulfonyl]carbamateHCID 198735293-Methyl-5-(2-thienyl)-2-pyrazoline

Product 1

HCID 198735301-[(N-dimethylsulfamoyl-N-methylamino)sulfonylcarbamoyl]-3-methyl-5-(2-thienyl)-2-pyrazolineYield 76.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture comprising 1.69 g (5.0 mmol) of phenyl N-[(N-dimethylsulfamoyl-N-methylamino)sulfonyl]carbamate, 0.58 g (3.5 mmol) of 3-methyl-5-(2-thienyl)-2-pyrazoline and 10 ml of dry benzene, was refluxed for 10 minutes. The mixture was left to cool, and then benzene was distilled off under reduced pressure. The obtained residue was washed with n-hexane. Then, the residue was stirred together with diethyl ether. The precipitated crystalline product was isolated by suction filtration and then washed with diethyl ether to obtain 1.1 g of the desired 1-[(N-dimethylsulfamoyl-N-methylamino)sulfonylcarbamoyl]-3-methyl-5-(2-thienyl)-2-pyrazoline.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. distillationbenzene was distilled off under reduced pressure
  4. washThe obtained residue was washed with n-hexane
  5. customThe precipitated crystalline product was isolated by suction filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7852223a462f4d96b9c43a3b7ce1ed21
Source dataset
uspto-grants-1992_10
Patent number
US05152824

Reaction notes

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