Methyl iodide → HCID 18630315, compound

HRID 378044Notes

Reaction equation

HRID 378044 reaction equation
[CH2:1]([N:3]([CH3:17])[C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:2].[C:18](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH2:1]([N:3]([CH3:17])[C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([CH3:18])[C:12]([CH3:13])([CH3:15])[CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18630229HCID 18630229, compound

Product 1

HCID 18630315HCID 18630315, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of N-ethyl-N-methyl 2-(N-tert-butylamino)benzamide (1.89 g, 8.1 mmol), potassium carbonate (2.2 g, 15.9 mmol), and methyl iodide (2.3 g, 16.2 mmol) in DMF (40 mL) was heated overnight at 40° C., then was partitioned between EtOAc and water. The EtOAc was dried (MgSO4), concentrated, and purified by HPLC with 1:4 ethyl acetate/cyclohexane to afford 1.923 g of N-ethyl-N-methyl 2-(N-methyl-N-tert-butylamino)benzamide as a yellow oil, a 96% yield.

Workup

  1. customwas partitioned between EtOAc and water
  2. dry with materialThe EtOAc was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by HPLC with 1:4 ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-803bede597b04501a010806a4521a673
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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