Water → N-(3-Cyano-phenyl)-4-methoxy-N-methyl-benzamide

HRID 578718Notes

Reaction equation

HRID 578718 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].[CH3:22]I.O>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:22])[C:10](=[O:19])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 904414N-(3-cyanophenyl)-4-methoxybenzamide

Product 1

HCID 47407961N-(3-Cyano-phenyl)-4-methoxy-N-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (1.9 mmol) N-(3-Cyano-phenyl)-4-methoxy-benzamide were dissolved in 25 ml THF and 150 mg sodium hydride (60% in oil, 3.7 mmol) were added. The reaction was stirred for 1 h at room temperature, 172 μl (2.8 mmol) methyl iodide were added and the mixture was stirred for 2 h at 60° C. To the reaction mixture water was added and subsequently extracted with ethyl acetate, dried over Na2SO4 and evaporated to dryness.

Workup

  1. stirringthe mixture was stirred for 2 h at 60° C
  2. extractionsubsequently extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a842cf2fecae4d3b9f48e90a3587f614
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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