1,2-Dichloroethane → N-Methoxy-2-(4-methoxyphenyl)-N-methylacetamide

HRID 1815988Notes

Reaction equation

HRID 1815988 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.Cl.[CH3:14][O:15][NH:16][CH3:17].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl>CN(C=O)C>[CH3:14][O:15][N:16]([CH3:17])[C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22496069N-Methoxy-2-(4-methoxyphenyl)-N-methylacetamideYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyphenylacetic acid (3.3 g, 20 mmole) in dry DMF (75 mL) was added N-methoxy-N-methylamine hydrochloride (1.95 g, 20 mmole), Et3N (3.1 mL, 22 mmole), HOBt H2O (1.95 g, 22 mmole), and EDC (2.7 g, 22 mmole). The solution was stirred at RT overnight, then was concentrated in vacuum. The residue was taken up in 5% Na2CO3 solution (10 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel (3% MeOH/CH2Cl2) to give the title compound (1.54 g, 37%) as white solid: MS (ES) m/e 210 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuum
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6ae97f10c7d64008b75643baebec4e4a
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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