Hydrochloric Acid → HCID 72359990, compound

HRID 2103911Notes

Reaction equation

HRID 2103911 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=[N:17][NH:18][C:19]([NH:21][C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=3)=[S:20])[CH3:16])[C:10]=2[OH:35])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].Cl.O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=[N:17][NH:18][C:19]([NH:21][C:22]3[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=3)=[S:20])[CH3:16])[C:10]=2[OH:35])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 72360033Methyl 4-{[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)-carbonothioyl]amino}-2-nitrobenzoate

Product 1

HCID 72359990HCID 72359990, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-{[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)-carbonothioyl]amino}-2-nitrobenzoate (100 mg, 0.19 mmol) synthesized in Synthetic Example 104 was dissolved in methanol (3 ml), and 1 M sodium hydroxide aqueous solution (0.74 ml, 0.74 mmol) was added thereto, following by stirring overnight at room temperature. After completion of the stirring, 1 M hydrochloric acid (0.74 ml, 0.74 mmol) and water were added thereto. The precipitated solid was recovered by filtration, washed with water, isopropyl alcohol, and chloroform. The obtained solid was stirred in chloroform, and then filtered to obtain 37 mg of the desired product as a yellow solid (yield 48%).

Workup

  1. filtrationThe precipitated solid was recovered by filtration
  2. washwashed with water, isopropyl alcohol, and chloroform
  3. stirringThe obtained solid was stirred in chloroform
  4. filtrationfiltered

Sources & evidence

ORD record
ord-974ff83d969d454ba87e3041edffc5ae
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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