Sodium Hydroxide → HCID 59631853, compound
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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]+.