Dimethylformamide → HCID 117724720, compound

HRID 628546Notes

Reaction equation

HRID 628546 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH3:18])[CH:9]=2)[CH:3]=1.[CH3:19]N(C)C=O.[H-].[Na+].S(OC)(OC)(=O)=O>O>[CH:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:3]=[C:2]([O:1][CH3:19])[N:6]([CH3:7])[N:5]=2)=[CH:9][C:10]=1[CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178422872HCID 178422872, compound

Product 1

HCID 117724720HCID 117724720, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, to mixture of 5-hydroxy-3-(4 isopropoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole (described in Reference Preparation example 95) 9.5 g, and N,N-dimethylformamide 70 ml was added 55%-sodium hydride 2.5 g and was stirred for one hour, and thereto was then added dimethyl sulfate 9.7 g and stirred at 100° C. for 12 hours. Thereto was added water 50 ml and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1-methyl-1H-pyrazole 5.8 g.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-33fffd68aef343d39ec6095805351be0
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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