Methyl iodide → 2-[[(1-Methylpyridinium-4-yl)carbonyl]amino]-N-(4-chlorophenyl)benzamide Iodide

HRID 395843Notes

Reaction equation

HRID 395843 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][C:10]2[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[O:13])=[O:8])=[CH:3][CH:2]=1.[CH3:26][I:27]>CN(C=O)C>[I-:27].[CH3:26][N+:1]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][C:10]2[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[O:13])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 1099265N-{2-[(4-chloroanilino)carbonyl]phenyl}isonicotinamide

Product 1

HCID 693592382-[[(1-Methylpyridinium-4-yl)carbonyl]amino]-N-(4-chlorophenyl)benzamide IodideYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-(4-pyridinecarbonyl)amino-N-(4-chlorophenyl)benzamide (500 mg, 1.42 mmol) in DMF (10 mL) was added methyl iodide (3 mL, 48 mmol). After 48 h, the precipitate was filtered, washed with diethyl ether and dried in vacuo to give 416 mg (59%) of the title compound.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-188efcd3d6c540ccaefca51e88697662
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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