Hydrochloric Acid → HCID 72359957, compound

HRID 1881598Notes

Reaction equation

HRID 1881598 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][CH:14]=[C:13]([C:16](=[N:18][NH:19][C:20]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)=[O:21])[CH3:17])[C:12]=2[OH:32])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][CH:14]=[C:13]([C:16](=[N:18][NH:19][C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)=[O:21])[CH3:17])[C:12]=2[OH:32])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 72360092HCID 72360092, compound

Product 1

HCID 72359957HCID 72359957, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoate (50 mg, 0.11 mmol) synthesized in Synthetic Example 35 was dissolved in methanol (1.1 mL) and stirred with 1 M aqueous sodium hydroxide (0.55 mL, 0.55 mmol) at 45° C. for 1.5 hours. After the stirring, 1 M hydrochloric acid (0.55 mL, 0.55 mmol) was added, and the precipitated pale yellow solid was recovered by filtration. The resulting solid was purified by silica gel chromatography (chloroform:methanol=9:1). The resulting solid was stirred with chloroform at room temperature and recovered by filtration to give the desired product as a pale yellow solid (11 mg, yield 23%).

Workup

  1. filtrationthe precipitated pale yellow solid was recovered by filtration
  2. customThe resulting solid was purified by silica gel chromatography (chloroform:methanol=9:1)
  3. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-f9e18e82313648bc938ef692493441bf
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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