Ethanol → [4-Phenyl-1-(4-tolyl)-3-pyrazolyl]-acetic acid ethyl ester

HRID 441849Notes

Reaction equation

HRID 441849 reaction equation
[C:1]1([C:7]2[C:8]([CH2:19][C:20](Cl)=[O:21])=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([OH:25])[CH3:24].N1C=CC=CC=1>C1C=CC=CC=1>[CH2:23]([O:25][C:20](=[O:21])[CH2:19][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:9]=1)[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 21418460[4-Phenyl-1-(4-tolyl)-3-pyrazolyl]-acetyl chloride

Product 1

HCID 13421310[4-Phenyl-1-(4-tolyl)-3-pyrazolyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2.2 g. of [4-phenyl-1-(4-tolyl)-3-pyrazolyl]-acetyl chloride crude product are reacted with 5 ml. of absolute benzene and 5 ml. of absolute ethanol. 0.2 ml. of pyridine are added dropwise to this mixture, which is allowed to stand at room temperature for 16 hours, and then diluted with 20 ml. of benzene. The reaction mixture then is washed in turn with water, diluted hydrochloric acid and water; dried and concentrated in vacuum. The residue is recrystallized from acetone/hexane. 1.7 g. of [4-phenyl-1-(4-tolyl)-3-pyrazolyl]-acetic acid ethyl ester with a melting point of 76°-79° C., is obtained.

Workup

  1. additiondiluted with 20 ml
  2. washThe reaction mixture then is washed in turn with water, diluted hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customThe residue is recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-82240a3b1d414b6da504efa5c3892944
Source dataset
uspto-grants-1977_08
Patent number
US04042706

Reaction notes

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