Triethylamine → n-(2,2-Dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 1380851Notes

Reaction equation

HRID 1380851 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](Cl)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH2:19].C(N(CC)CC)C>C(Cl)Cl>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH:19][C:12](=[O:13])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 13092500n-(2,2-Dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While cooling with ice, a solution of 3,4-dimethoxyphenylacetyl chloride (485.2 g) in methylene chloride (1.1 liters) is added dropwise at 15°-20° C. to a solution of aminoacetaldehyde dimethyl acetal (246.2 ml) and triethylamine (315 ml) in methylene chloride (2.2 liters) and the mixture is stirred for one hour at 16°-18° C. It is then extracted several times with water, dried over magnesium sulphate and concentrated by evaporation. The oil obtained slowly crystallizes out. Yield: 608 g. Mp: 66°-69° C.

Workup

  1. temperatureWhile cooling with ice
  2. extractionIt is then extracted several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe oil obtained slowly
  6. customcrystallizes out

Sources & evidence

ORD record
ord-a8114fe14c754d478dcd67a4b5eec680
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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