Phosphorus oxychloride → 5-Chloro-1-methyl-3-phenyl-1H-pyrazole

HRID 1659161Notes

Reaction equation

HRID 1659161 reaction equation
[CH3:1][N:2]1[C:6](=O)[CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:3]1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 27635041-methyl-3-phenyl-1H-pyrazol-5-ol

Product 1

HCID 126657925-Chloro-1-methyl-3-phenyl-1H-pyrazoleYield 96.8%

Procedure

2-Methyl-5-phenylpyrazol-3-one (7.9 g, 0.0429 mol) is added to phosphorus oxychloride (15.3 g). The mixture is stirred at 120°C to 135°C for 8 hours, then poured into ice water, made alkaline and extracted with methylene chloride. The solution is evaporated in vacuo at 90°C to yield 8.0 g (93.8%) of an oil.

Workup

  1. extractionextracted with methylene chloride
  2. customThe solution is evaporated in vacuo at 90°C

Sources & evidence

ORD record
ord-de7a0f14238246509b70e21123730f73
Source dataset
uspto-grants-1976_06
Patent number
US03966954

Reaction notes

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