Dimethylformamide → Methyl 4-{[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)-carbonothioyl]amino}-2-nitrobenzoate

HRID 1881642Notes

Reaction equation

HRID 1881642 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20](=O)[CH3:21])[C:15]=2[OH:23])[CH:10]=[CH:11][C:12]=1[Cl:13].[NH:24]([C:26]([NH:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]([N+:39]([O-:41])=[O:40])[CH:30]=1)=[S:27])[NH2:25]>Cl.O>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20](=[N:25][NH:24][C:26]([NH:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]([N+:39]([O-:41])=[O:40])[CH:30]=3)=[S:27])[CH3:21])[C:15]=2[OH:23])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 60206780HCID 60206780, compoundHCID 86014590Methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate

Product 1

HCID 72360033Methyl 4-{[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)-carbonothioyl]amino}-2-nitrobenzoateYield 92.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

Dimethylformamide (1 ml) and conc. hydrochloric acid (1 drop) were added to 1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (60 mg, 0.21 mmol) synthesized in Synthetic Example 1 and methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate (57 mg, 0.21 mmol) synthesized in Reference Synthetic Example 56, and the mixture was stirred at room temperature for 21 hours. Water was added, and the precipitated solid was filtered, purified with a silica gel column chromatography (n-hexane/ethyl acetate=1/1 then chloroform/methanol=95/5). The obtained solid was extracted with ethyl acetate, washed with a saturated ammonium chloride aqueous solution, saturated sodium chloride aqueous solution. The organic layer was concentrated to obtain the desired product as a pale yellow solid (104 mg, yield 92%).

Workup

  1. customsynthesized in Reference Synthetic Example 56
  2. filtrationthe precipitated solid was filtered
  3. custompurified with a silica gel column chromatography (n-hexane/ethyl acetate=1/1
  4. extractionThe obtained solid was extracted with ethyl acetate
  5. washwashed with a saturated ammonium chloride aqueous solution, saturated sodium chloride aqueous solution
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a9109dc970be40a88edd15fe27edfaf7
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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