3-Chloro-2-methylaniline → N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamide

HRID 1009464Notes

Reaction equation

HRID 1009464 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:19]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][CH2:17][C:18]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 68943-Chloro-2-methylanilineHCID 11430Potassium CarbonateHCID 467366912-Bromo-N-(4-methoxybenzyl)acetamide

Product 1

HCID 26417493N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamideYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.93 g of 3-chloro-2-methylaniline was dissolved in 10 mL of DMF, and 2.00 g of potassium carbonate was added thereto, followed by portionwise addition of 3.55 g of 2-bromo-N-(4-methoxybenzyl)acetamide over 1 hour. The mixture was stirred at room temperature overnight, and ice water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30 to 30:70) to obtain 2.89 g of N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamide.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30 to 30:70)

Sources & evidence

ORD record
ord-487d1c7550d14bbda2bcd20b348ee1ee
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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