(3,4-Dimethoxyphenyl)acetic acid → n-(2,2-Dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 2286387Notes

Reaction equation

HRID 2286387 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C1(N=C=NC2CCCCC2)CCCCC1.[C:23](O)(=[O:35])[CH2:24][C:25]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=1>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:23](=[O:35])[CH2:24][C:25]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=1

Participants

5

Reactant 3

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 10868DicyclohexylcarbodiimideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of aminoacetaldehyde dimethylacetal (21 g., 0.2 mole) and dicyclohexylcarbodimide (42.5 g., 0.205 mole) in 500 ml. of methylene chloride was added homoveratric acid (39.2 g., 0.2 mole) portionwise with cooling and stirring. After the addition was completed, the reaction mixture was stirred at room temperature for 1/2 hour, kept in refrigerator overnight and filtered. The filtrate was evaporated to dryness to give an oil which was chilled to form the solid N-(2,2-dimethoxyethyl)-3,4-dimethoxyphenylacetamide, m.p. 60°-63° C.

Workup

  1. temperaturewith cooling
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred at room temperature for 1/2 hour
  4. customkept in refrigerator overnight
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customto give an oil which
  8. temperaturewas chilled

Sources & evidence

ORD record
ord-5da3087aef104f2cb069237112feb529
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

Loading…