Dimethyl Sulfate → HCID 11357876, compound

HRID 2182807Notes

Reaction equation

HRID 2182807 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[NH:10][N:9]=2)=[C:4]([F:17])[CH:3]=1.S(OC)(O[CH3:22])(=O)=O.[NH4+].[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]([O:13][CH:14]([F:16])[F:15])[N:10]([CH3:22])[N:9]=2)=[C:4]([F:17])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 25517Ammonium ChlorideHCID 1785058263-(4-chloro-2-fluorophenyl)-5-difluoromethoxy-1H-pyrazole

Product 1

HCID 11357876HCID 11357876, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11.6 g of the 3-(4-chloro-2-fluorophenyl)-5-difluoromethoxy-1H-pyrazole (purity 86%) obtained in step 1.2 were initially charged in 100 ml of toluene. 6.2 g of dimethyl sulfate were added dropwise, and the mixture was heated at reflux for 3 h. After cooling, 25 ml of saturated aqueous NH4Cl solution were added, the mixture was stirred for 1 h and the organic phase was separated off and washed with water until neutral. Drying over Na2SO4 and concentration gave 11.3 g of 3-(4-chloro-2-fluorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole as an oil of a purity of 82.4% (GC). Yield: 88.6%

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. customthe organic phase was separated off
  5. washwashed with water until neutral
  6. dry with materialDrying over Na2SO4 and concentration

Sources & evidence

ORD record
ord-281d408c6d9f4d0eb2192145ed3d1142
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

Loading…