Potassium Carbonate → N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide

HRID 1655887

Reaction equation

HRID 1655887 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:4].[CH3:15][N:16]1[C:20]([CH3:21])=[CH:19][C:18]([C:22](Cl)=[O:23])=[N:17]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:22]([C:18]1[CH:19]=[C:20]([CH3:21])[N:16]([CH3:15])[N:17]=1)=[O:23])(=[O:13])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 42546Benzoic acid, 2-(aminosulfonyl)-, methyl esterHCID 27763641,5-Dimethyl-1H-Pyrazole-3-Carbonyl Chloride

Product 1

HCID 19789275N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamideYield 68.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.8 g of 2-methoxycarbonylphenylsulfonamide, 8.6 g of 1,5-dimethylpyrazole-3-carbonyl chloride and 13.8 g of potassium carbonate in 200 ml of absolute acetone are refluxed for 8 h. The solvent is removed by distillation and then the residue is taken up in water and the pH is adjusted to 2. The precipitate is filtered off with suction and washed with H2O until neutral. The residue is stirred with ether, filtered off with suction and dried under reduced pressure. 11.6 g of N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide with a melting point of 176°-177° C. are obtained (active ingredient Example No. 40).

Workup

  1. customThe solvent is removed by distillation
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed with H2O until neutral
  4. filtrationfiltered off with suction
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-e5e328d007e548d3853bd9f38157dfaa
Source dataset
uspto-grants-1993_10
Patent number
US05252540

Linked notes

Loading…