Sodium Hydroxide → 5-[(2-{1-[5-(3,4-Dichlorophenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylic acid

HRID 2103885Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 72359944Methyl 5-[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylate

Product 1

HCID 731529555-[(2-{1-[5-(3,4-Dichlorophenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylic acidYield 13.7%

Procedure

From methyl 5-[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylate (56.3 mg, 0.12 mmol) and 0.2 M sodium hydroxide aqueous solution (1.89 mL, 0.38 mmol), 7.5 mg of the desired product was obtained in the same manner as in Synthetic Example 66 as a pale yellow solid (yield 14%).

Sources & evidence

ORD record: ord-0146c93cfe1146a69e055aaed2428d5d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576115B2

Reaction notes

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