Methyl iodide → HCID 70221463, compound

HRID 582001Notes

Reaction equation

HRID 582001 reaction equation
[N:1]1([CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]3)[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].I[CH3:31]>CN(C)C=O>[CH3:31][N:13]1[C:14]2[C:9](=[CH:8][C:7]([CH:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=3)=[CH:16][CH:15]=2)[CH:10]=[CH:11][C:12]1=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 49824866HCID 49824866, compound

Product 1

HCID 70221463HCID 70221463, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 3 (10 g) in N,N-dimethylformamide (100 ml) was stirred at room temperature under N2. Sodium hydride (0.51 g) was added portionwise and the mixture was stirred for 15 minutes. The mixture was cooled, iodomethane was added dropwise and the reaction mixture was stirred for 12 hours. The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The separated organic layer was dried over MgSO4, filtered and the filtrate evaporated. The oily residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from methyl ethyl keton/diethyl ether, yielding 2.9 g(28%) (±)-1methyl-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl)phenyl]methyl]-2(1H)-quinolinone (compound 12; mp. 186.7° C.). In a similar manner, the following compounds were prepared:

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. temperatureThe mixture was cooled
  3. stirringthe reaction mixture was stirred for 12 hours
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between CH2Cl2 and water
  6. dry with materialThe separated organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. customThe oily residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from methyl ethyl keton/diethyl ether

Sources & evidence

ORD record
ord-72bef0cd8c3b494b8f100ca83a8e683a
Source dataset
uspto-grants-1999_07
Patent number
US05922734

Reaction notes

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