Sodium Hydroxide → HCID 19789276, compound

HRID 1655888Notes

Reaction equation

HRID 1655888 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[S:27]([NH2:30])(=[O:29])=[O:28].[OH-].[Na+]>ClCCCl.C(N(CC)CC)C>[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[S:27]([NH:30][C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9])(=[O:29])=[O:28]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 728812-ThiophenesulfonamideHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 19789276HCID 19789276, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

3.8 g of 1-methylpyrazole-4-carboxylic acid and 4.9 g of carbonyldiimidazole in 100 ml of 1,2-dichloroethane are heated at 55° C. for 3.5 h. 4.9 g of 2-thienylsulfonamide and 5.4 ml of triethylamine are added and then the mixture is heated at 55° C. for 13 h. After cooling, 40 ml of 10% strength aqueous NaOH solution are added and then the pH of the aqueous phase is adjusted to 1. The precipitate is removed and dried under reduced pressure. 5.2 g of N-(2-thienylsulfonyl)-1-methylpyrazole-4-carboxamide with a melting point of 174°-180° C. are obtained (active ingredient Example No. 103).

Workup

  1. temperatureAfter cooling
  2. customThe precipitate is removed
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-eb1c184496fa44b590c2833c1219fdd5
Source dataset
uspto-grants-1993_10
Patent number
US05252540

Reaction notes

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