Water → HCID 23508555, compound

HRID 1883685Notes

Reaction equation

HRID 1883685 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH3:23]I.O>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH3:23])=[O:8])=[CH:19][CH:20]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 8023087HCID 8023087, compound

Product 1

HCID 23508555HCID 23508555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

79 mg of 4-cyano-N-(4-methoxybenzyl)benzamide was dissolved in 2.5 ml of tetrahydrofuran, and 24 mg of 60% sodium hydride was added thereto, followed by heating under reflux for 5 minutes in an atmosphere of nitrogen. After cooling, 0.1 ml of methyl iodide was added thereto, followed by stirring for 15 minutes. Thereafter, the reaction was stopped by the addition of 1 ml of distilled water. After the product was extracted with ethyl acetate, the extract was successively washed with 2 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by TLC (using a 1:1 mixture of ethyl acetate and hexane as the developing solvent) to obtain 72 mg of 4-cyano-N-(4-methoxybenzyl)-N-methylbenzamide.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 minutes in an atmosphere of nitrogen
  3. temperatureAfter cooling
  4. extractionAfter the product was extracted with ethyl acetate
  5. washthe extract was successively washed with 2 N hydrochloric acid
  6. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe resulting crude product was purified by TLC (
  9. additiona 1:1 mixture of ethyl acetate and hexane as the developing solvent)

Sources & evidence

ORD record
ord-86e9f46cc3724cd3ae547381185a4991
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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