Sodium Hydroxide → HCID 59631853, compound

HRID 2369040Notes

Reaction equation

HRID 2369040 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=3)=[CH:13][CH:14]=2)[N:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[N:6]=1)=[O:4].[OH-].[Na+]>CO>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[N:7]1[C:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:16]=3)=[CH:13][CH:14]=2)=[CH:9][C:5]([C:3]([OH:4])=[O:2])=[N:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59631939HCID 59631939, compound

Product 1

HCID 59631853HCID 59631853, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-(2-chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazole-3-carboxylic acid methyl ester (5.8 g, 123 mmol) in MeOH (50 mL) was added aqueous NaOH (4 N, 25 mL) and the mixture was refluxed for 2 h. After cooling to 20° C., solvent was removed. Water was added to dissolve the crude and then the solution was acidified with acetic acid. Solid was collected by filtration and washed with water and dried under high vacuum to give 1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazole-3-carboxylic acid (5.1 g). MS(ES): 459 [M+H]+.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customsolvent was removed
  3. additionWater was added
  4. dissolutionto dissolve the crude
  5. filtrationSolid was collected by filtration
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-d54decbe437c49c1ba02bf52a65eab83
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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