Ammonia → HCID 178481735, compound

HRID 2182813Notes

Reaction equation

HRID 2182813 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:13]=[C:12]([OH:14])[NH:11][N:10]=1.S(OC)(O[CH3:19])(=O)=O.C(=O)([O-])[O-].[K+].[K+].N.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:13]=[C:12]([OH:14])[N:11]([CH3:19])[N:10]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178515597HCID 178515597, compound

Product 1

HCID 178481735HCID 178481735, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 g of 3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazole from Example 3.1 were initially charged in 750 ml of toluene. 23.1 g of dimethyl sulfate and 7.5 g of potassium carbonate were added, and the mixture was heated at reflux for 2 h. After cooling to room temperature, the mixture was made alkaline using ammonia and stirred overnight. The mixture was acidified by addition of hydrochloric acid (pH about 1) and cooled to room temperature, and the precipitated solid was filtered off. Drying gave 21.4 g of 3-(2,4-dichlorophenyl)-5-hydroxy-1-methyl-1H-pyrazole (purity according to GC 99.2%, yield 66.8%). M.p.: 128° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled to room temperature
  4. filtrationthe precipitated solid was filtered off
  5. customDrying

Sources & evidence

ORD record
ord-7699cd7ee4c345c598cec46a2ba68854
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

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