Benzenepropanoyl chloride → 5-Phenyl-3-(3-phenylpropionyl)aminopyrazole

HRID 567793Notes

Reaction equation

HRID 567793 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.[C:13]1([CH2:19][CH2:20][C:21](Cl)=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:7]1([C:5]2[NH:4][N:3]=[C:2]([NH:1][C:21](=[O:22])[CH2:20][CH2:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 154897545-Phenyl-3-(3-phenylpropionyl)aminopyrazole

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-5-phenylpyrazole (160 mg) was dissolved in pyridine (1 ml) to which was subsequently added 3-phenylpropionyl chloride (0.15 ml), and the mixture was stirred at room temperature for 14 hours and then at 50° C. for 30 minutes. The reaction solution was diluted with ethyl acetate (15 ml), washed with water (15 ml), 10% citric acid (15 ml), 1 N aqueous sodium hydroxide solution (15 ml) and saturated brine (15 ml) and then dried over anhydrous sodium sulfate. The solvent was distilled away under a reduced pressure, and the resulting residue was crystallized from ethanol to obtain the title compound (139 mg) as white crystals (melting point: 168 −170° C.).

Workup

  1. waitat 50° C. for 30 minutes
  2. washwashed with water (15 ml), 10% citric acid (15 ml), 1 N aqueous sodium hydroxide solution (15 ml) and saturated brine (15 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under a reduced pressure
  5. customthe resulting residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f9de44c989234c88b13bca95f8b2539d
Source dataset
uspto-grants-2001_01
Patent number
US06180653B2

Reaction notes

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