Methyl iodide → HCID 16063633, compound

HRID 1993936Notes

Reaction equation

HRID 1993936 reaction equation
[C:1]12([C:11]3[C:12](=[O:22])[NH:13][N:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.I[CH3:24]>CN(C=O)C>[C:1]12([C:11]3[C:12](=[O:22])[N:13]([CH3:24])[N:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:15]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 16063632HCID 16063632, compound

Product 1

HCID 16063633HCID 16063633, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sealable tube was charged with 4-adamantan-1-yl-1-phenyl-1,2-dihydro-pyrazol-3-one (0.05 g), iodomethane (0.036 g) and DMF (1 mL) and purged with argon and sealed. The reaction vessel was immersed into a heated oil bath at 110 degrees C. for 16 hours. The reaction vessel was then cooled and opened carefully. The reaction mixture was diluted with EtOAc and aqueous sodium bicarbonate solution and the phases were separated. The aqueous layer was extracted with further EtOAc and the combined organic layers were washed with sodium thiosulfate. The phases were then dried over sodium sulfate, filtered and reduced in vacuo. The crude gum was chromatographed by adsorption onto silica gel and subjection to Isco Combiflash chromatography. Evaporation of the desired fractions afforded the desired product 4-adamantan-1-yl-2-methyl-1-phenyl-1,2-dihydro-pyrazol-3-one (0.035 mg) as a white solid. MS (ESI+): 309.4 [M+H]+).

Workup

  1. custompurged with argon
  2. customsealed
  3. customThe reaction vessel was immersed into a heated oil bath at 110 degrees C
  4. temperatureThe reaction vessel was then cooled
  5. additionThe reaction mixture was diluted with EtOAc and aqueous sodium bicarbonate solution
  6. customthe phases were separated
  7. extractionThe aqueous layer was extracted with further EtOAc
  8. washthe combined organic layers were washed with sodium thiosulfate
  9. dry with materialThe phases were then dried over sodium sulfate
  10. filtrationfiltered
  11. customThe crude gum was chromatographed by adsorption onto silica gel and subjection to Isco Combiflash chromatography
  12. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-938dae0e71774f3f8963df1f5bd84d18
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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