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

HRID 1154630Notes

Reaction equation

HRID 1154630 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 485.2 gm of 3,4-dimethoxyphenyl-acetic acid chloride in 1.1 liters of methylene chloride at 15° C. to 20° C. was added dropwise to a solution of 246.2 ml of aminoacetaldehyde dimethyl acetal and 315 ml of triethylamine in 2.2 liters of methylene chloride, and the mixture was stirred for one hour at 16° to 18° C. Then, it was extracted with water several times, dried over magnesium sulfate and concentrated by evaporation. The oil thus obtained slowly crystallized.

Workup

  1. temperatureWhile cooling with ice
  2. extractionThen, it was extracted with water several times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe oil thus obtained slowly
  6. customcrystallized

Sources & evidence

ORD record
ord-08e2719df8a845c998c2d75352cba400
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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