Ammonia → HCID 178481736, compound

HRID 2182808Notes

Reaction equation

HRID 2182808 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[NH:10][N:9]=2)=[C:4]([F:14])[CH:3]=1.S(OC)(O[CH3:19])(=O)=O.N.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([CH3:19])[N:9]=2)=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 178515601HCID 178515601, compound

Product 1

HCID 178481736HCID 178481736, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 g of 3-(4-chloro-2-fluorophenyl)-5-hydroxy-1H-pyrazole from Example 1.1 were initially charged in 1500 ml of toluene. 35.5 g of dimethyl sulfate were then added, and the mixture was heated at reflux for 3 h. After cooling to room temperature, the mixture was made alkaline using ammonia, stirred overnight and acidified by addition of hydrochloric acid. The mixture was then cooled to 0° C., and the precipitated solid was filtered off. After drying, 49.4 g of 3-(4-chloro-2-fluorophenyl)-5-hydroxy-1-methyl-1H-pyrazole were obtained as crude product (purity according to NMR about 80%, impurity essentially starting material), which was purified by recrystallization from toluene to >95% purity. Yield 49.4 g, 74.1%. M.p.: 204° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was then cooled to 0° C.
  4. filtrationthe precipitated solid was filtered off
  5. customAfter drying

Sources & evidence

ORD record
ord-9312b4154e1442d3a3c0dfc1bbc0214d
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

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