Chloromethyl Methyl Ether → HCID 15451919, compound

HRID 378211Notes

Reaction equation

HRID 378211 reaction equation
[H-].[Na+].[C:3]([C:11]1[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[N:13][NH:14][CH:15]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23][O:24][CH2:25]Cl>CN(C)C=O>[C:3]([C:11]1[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[N:13][N:14]([CH2:23][O:24][CH3:25])[CH:15]=1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178519494HCID 178519494, compound

Product 1

HCID 15451919HCID 15451919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 55% sodium hydride (1.9 g) was added N,N-dimethylformamide (3 ml) and stirred while cooled with ice. To this was then added dropwise a solution of 4-benzoyl-3-(3-chlorophenyl)pyrazole (1.24 g) in N,N-dimethylformamide. The reaction mixture was stirred for 20 minutes at room temperature after the vigorous foaming ceased. The reaction mixture was added with chloromethyl methyl ether (0.59 g) and stirred for 5 hours at room temperature, which was then poured into ice-water, extracted with ethyl acetate, washed with water and dried on anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The thus obtained residue was purified by column chromatography (silica gel; ethyl acetate/n-hexane=3/1) and recrystallized from acetonitrile to give the compound of interest (620 mg). M.P.: 105.5-107.9° C.

Workup

  1. temperaturewhile cooled with ice
  2. stirringThe reaction mixture was stirred for 20 minutes at room temperature after the vigorous foaming
  3. stirringstirred for 5 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried on anhydrous sodium sulfate
  7. distillationthe solvent was then distilled off under reduced pressure
  8. customThe thus obtained residue was purified by column chromatography (silica gel; ethyl acetate/n-hexane=3/1)
  9. customrecrystallized from acetonitrile
  10. customto give the compound of interest (620 mg)

Sources & evidence

ORD record
ord-522adfe1a55746d9a11608603cb43a44
Source dataset
uspto-grants-2000_02
Patent number
US06030926

Reaction notes

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