Sodium Hydroxide → HCID 59631853, compound

HRID 2369065Notes

Reaction equation

HRID 2369065 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)=[CH:15][CH:16]=2)[N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:8]=1)=[O:6]>CO>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:9]1[C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:18]=3)=[CH:15][CH:16]=2)=[CH:11][C:7]([C:5]([OH:6])=[O:4])=[N:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59631939HCID 59631939, compound

Product 1

HCID 59631853HCID 59631853, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous NaOH solution (2N, 80 mL) was added to a suspension of 1-(2-chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazole-3-carboxylic acid methyl ester (5 g, 10.57 mmol) in MeOH (80 mL), and the resulting mixture was stirred at reflux for 10 h. The volatiles was removed in vacuo, the residual solution was acidified with aqueous HCl (6N) to pH 2, extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The crude product was recrystallized from DCM/hexane to give the title compound as a white solid (4.1 g, 86%). 1H-NMR (DMSO-d6): δ 12.73 (s, 1H), 7.98 (m, 1H), 7.83 (m, 2H), 7.77 (m, 2H), 7.71 (m, 1H), 7.67 (d, 1H), 7.62 (m, 2H), 7.34 (s, 1H), 7.19 (s, 1H), 3.26 (s, 3H). MS(ES): 459 [M+H]+.

Workup

  1. temperatureat reflux for 10 h
  2. customThe volatiles was removed in vacuo
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customThe crude product was recrystallized from DCM/hexane

Sources & evidence

ORD record
ord-6c55271f020646eba5b77ae767a29687
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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