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

HRID 364068Notes

Reaction equation

HRID 364068 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-dimethoxyphenylacetic acid chloride (485.2 g) in methylene chloride (1.1 liters) is added dropwise at 15° to 20° C. to a solution of aminoacetaldehyde dimethylacetal (246.2 ml) and triethylamine (315 ml) in methylene chloride (2.2 liters) of and the mixture is stirred for 1 hour at 16°-18° C. It is then extracted several times with water, dried over magnesium sulphate and evaporated. The oil obtained slowly crystallizes out.

Workup

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

Sources & evidence

ORD record
ord-01aca9907c9f4eeaa3fac565ccc4cb82
Source dataset
uspto-grants-1986_08
Patent number
US04604389

Reaction notes

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