Methyl iodide → HCID 18630199, compound

HRID 356437Notes

Reaction equation

HRID 356437 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[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:19](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH2:17]([N:3]([CH2:1][CH3:2])[C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([CH3:19])[C:12]([CH3:13])([CH3:15])[CH3:14])[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 13296791HCID 13296791, compound

Product 1

HCID 18630199HCID 18630199, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of N,N-diethyl-2-(N-tert-butylamino)benzamide (4.2 g, 17 mmol), potassium carbonate (3.1 g, 22 mmol), and MeI (3.1 g, 22 mmol) in DMF (75 mL) was heated overnight at 40° C. The reaction was not complete, so additional MeI (3.1 g, 22 mmol) was added and the reaction heated at 40° C. for 1 d, 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 3.22 g of N,N-diethyl-2-(N-methyl-N-tert-butylamino)benzamide as a yellow oil, a 72% yield.

Workup

  1. temperaturethe reaction heated at 40° C. for 1 d
  2. customwas partitioned between EtOAc and water
  3. dry with materialThe EtOAc was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by HPLC with 1:4 ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-3c48a7b1516b41fba5bfdd0e8dd1e396
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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