Sodium Hydroxide → HCID 72360053, compound

HRID 2103909Notes

Reaction equation

HRID 2103909 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17](=[N:19][NH:20][C:21]([NH:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[C:26]([N+:34]([O-:36])=[O:35])[CH:25]=3)=[S:22])[CH3:18])[C:12]=2[OH:37])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17](=[N:19][NH:20][C:21]([NH:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[C:26]([N+:34]([O-:36])=[O:35])[CH:25]=3)=[S:22])[CH3:18])[C:12]=2[OH:37])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 72360067HCID 72360067, compound

Product 1

HCID 72360053HCID 72360053, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-{[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)-carbonothioyl]amino}-2-nitrobenzoate (100 mg, 0.19 mmol) synthesized in Synthetic Example 102 was dissolved in methanol (6.7 ml), and 1 M sodium hydroxide aqueous solution (0.96 ml, 0.96 mmol) was added thereto, following by stirring overnight at room temperature. After completion of the stirring, the reaction solution was washed with ethyl acetate, and to the aqueous layer, 1 M hydrochloric acid was added. The precipitated solid was filtered to obtain 27 mg of the desired product as a pale yellow solid (yield 28%).

Workup

  1. washAfter completion of the stirring, the reaction solution was washed with ethyl acetate
  2. additionto the aqueous layer, 1 M hydrochloric acid was added
  3. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-cecd6b82bd0340f0b18b0890c3cbfebf
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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