Hydrazine hydrate (1:1) → HCID 940183, compound

HRID 1498928Notes

Reaction equation

HRID 1498928 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([C:14]([OH:16])=O)[NH:12][N:13]=1.O.[NH2:18][NH2:19]>CO.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([C:14]([NH:18][NH2:19])=[O:16])[NH:12][N:13]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9451245-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 940183HCID 940183, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

In methanol (20 ml), 5-(2,4-dichlorophenyl)-2H-pyrazole-3-carboxylic acid (1.00 g) was dissolved, and 6 drops of concentrated sulfuric acid was added thereto. The mixture was heated under reflux for 19 hours. After the mixture was allowed to cool, hydrazine monohydrate (0.97 g) was added to the mixture, and the resulting mixture was heated under reflux for 16 hours. The mixture was concentrated under a reduced pressure, and water was added thereto. The precipitated crystal was separated by filtration, washed with water, and dried to give the title compound (912 mg, 87%) as a white powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 19 hours
  3. temperatureto cool
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 16 hours
  6. concentrationThe mixture was concentrated under a reduced pressure, and water
  7. additionwas added
  8. customThe precipitated crystal was separated by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-4818ad5150814f3fb1109d6d6d20937c
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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