Hydrochloric Acid → 2-Acetamino-4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoic acid

HRID 2103883Notes

Reaction equation

HRID 2103883 reaction equation
[NH:1]([C:5]1[CH:14]=[C:13]([C:15]([NH:17][N:18]=[C:19]([C:21]2[C:25]([OH:26])=[C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=3)[S:23][CH:22]=2)[CH3:20])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8])[C:2]([CH3:4])=[O:3].[OH-].[Na+].Cl>C(O)(C)C>[NH:1]([C:5]1[CH:14]=[C:13]([C:15]([NH:17][N:18]=[C:19]([C:21]2[C:25]([OH:26])=[C:24]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:31][CH:32]=3)[S:23][CH:22]=2)[CH3:20])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86604757Methyl 2-acetamino-4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoate

Product 1

HCID 866047582-Acetamino-4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoic acidYield 35.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of methyl 2-acetamino-4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}-hydrazino)carbonyl]benzoate (50.8 mg, 0.1 mmol) in isopropyl alcohol (1.0 mL), 0.2 M sodium hydroxide aqueous solution (1.1 mL, 0.22 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After completion of the stirring, 1 M hydrochloric acid (220 μL) was added, and the precipitated solid was filtered and then washed with methanol to obtain 17.5 mg of the desired product as a pale yellow solid (yield 35%).

Workup

  1. additionwas added
  2. filtrationthe precipitated solid was filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-5d3a02ecb62e4d6bac432dd5e7118fb6
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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