Hydrochloric Acid → 3-Amino-4-(4-benzylphenyl)-2-carbamoylpyrazole

HRID 439778Notes

Reaction equation

HRID 439778 reaction equation
[CH:1]([CH:3]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)[C:4]#[N:5])=O.Cl.[NH2:20][NH:21][C:22]([NH2:24])=[O:23].[OH-].[Na+].Cl>O.CO>[NH2:5][C:4]1[N:21]([C:22](=[O:23])[NH2:24])[N:20]=[CH:1][C:3]=1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11236Semicarbazide hydrochlorideHCID 14798Sodium HydroxideHCID 15280468alpha-Formyl-4-benzylphenylacetonitrile

Product 1

HCID 152804693-Amino-4-(4-benzylphenyl)-2-carbamoylpyrazoleYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of α-formyl-4-benzylphenylacetonitrile (152.22 g), semicarbazide hydrochloride (72.24 g), methanol (400 ml) and water (80 ml) was stirred at room temperature, and after 18 hours, maintained pH to about 10 with 5N sodium hydroxide aqueous solution. When heat was generated, the reaction mixture was cooled with ice-water. After stirring at room temperature for 1 hour, the reaction mixure was neutralized with 10% hydrochloric acid, and water (1 l) was added. After stirring for 1 hour, the precipitate was separated by filtration, washed with water, and dried to give the title compound (165.52 g).

Workup

  1. temperaturemaintained
  2. temperatureWhen heat
  3. stirringAfter stirring at room temperature for 1 hour
  4. additionwas added
  5. stirringAfter stirring for 1 hour
  6. customthe precipitate was separated by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b8189ceee0a44e8383475cd5fdaf03eb
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

Loading…