Methyl iodide → HCID 19428751, compound

HRID 1079105Notes

Reaction equation

HRID 1079105 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]([NH:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].CI.[C:27](OCC)(=O)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]([N:14]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[CH3:27])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19428752HCID 19428752, compoundHCID 22728543Water ethylacetate

Product 1

HCID 19428751HCID 19428751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of N,N-dimethylformamide was dissolved 1.5 g of 4-(4-chlorobenzyloxy)-N-cyclopropylmethylbenzamide. To the solution was added 0.25 g of sodium hydride. The mixture was stirred at room temperature for 30 minutes and then at 60° C. for 30 minutes. The reaction mixture was ice-cooled, and 0.5 ml of methyl iodide was added thereto. The mixture was stirred overnight at room temperature. The reaction mixture was treated with ethyl acetate-water. The resulting ethyl acetate layer was separated, washed with water, dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent. The resulting residue was purified by column chromatography (eluant: dichloromethane/acetone=50/1) to obtain 1.4 g of 4-(4-chlorobenzyloxy)-N-cyclopropylmethyl-N-methylbenzamide.

Workup

  1. waitat 60° C. for 30 minutes
  2. temperaturecooled
  3. stirringThe mixture was stirred overnight at room temperature
  4. customThe resulting ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationsubjected to distillation
  8. customto remove the solvent
  9. customThe resulting residue was purified by column chromatography (eluant: dichloromethane/acetone=50/1)

Sources & evidence

ORD record
ord-44277d62f8934084a34b255933d4209c
Source dataset
uspto-grants-1996_08
Patent number
US05550292

Reaction notes

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