Methyl iodide → HCID 68468540, compound

HRID 502999Notes

Reaction equation

HRID 502999 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([C:17]3[N:21]([CH3:22])[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])=[N:19][N:18]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1.[CH3:30]I>CN(C=O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:30])[C:11]([C:13]2([C:17]3[N:21]([CH3:22])[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])=[N:19][N:18]=3)[CH2:14][CH2:15][CH2:16]2)=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11603730HCID 11603730, compound

Product 1

HCID 68468540HCID 68468540, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (55% oily, 13 mg) was suspended in DMF (3 ml) and then N-(4-chlorophenyl)-1-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]cyclobutanecarboxamide was added thereto under ice cooling, followed by stirring at room temperature for 30 minutes. Methyl iodide (17 μl) was added thereto under ice cooling, followed by stirring at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate (30 ml) and washed with a saturated sodium bicarbonate solution (10 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography (methanol:chloroform=2:98) to obtain 83 mg of N-(4-chlorophenyl)-1-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-N-methylcyclobutanecarboxamide (white solid).

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. washwashed with a saturated sodium bicarbonate solution (10 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography (methanol:chloroform=2:98)

Sources & evidence

ORD record
ord-f9b4d1b3c419438485074ee16b4a0a80
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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