Water → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxylic acid

HRID 839238

Reaction equation

HRID 839238 reaction equation
N(OS(=O)(=O)O)=[O:2].[N+:8]([C:11]1[O:15][C:14]([C:16]2[C:20]([C:21](N)=[O:22])=[CH:19][N:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9].O>P(=O)(O)(O)O>[N+:8]([C:11]1[O:15][C:14]([C:16]2[C:20]([C:21]([OH:2])=[O:22])=[CH:19][N:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 82157Nitrosylsulfuric acidHCID 203261233-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxamide

Product 1

HCID 203259643-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

Add 36 g of 98% nitrosylsulfuric acid (under cooling with ice) dropwise to a suspension of 50 g 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxamide in 830 ml of 89% orthophosphoric acid, whereupon the temperature rises from 0° C to 35° C. Stir the resulting reaction mixture for 18 hours at room temperature and pour the produced solution onto 5 kg of ice and water. Separate the formed precipitate and wash it with water until it is no longer acid to obtain a 98% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid [m.p. 264° to 265.5° C (with decomposition) from dioxane].

Workup

  1. customrises from 0° C to 35° C
  2. customthe resulting reaction mixture for 18 hours at room temperature
  3. customSeparate the formed precipitate
  4. washwash it with water until it

Sources & evidence

ORD record
ord-d72558aeda8b436aa12c823a1e0915d3
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Linked notes

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