Methoxyacetic Acid → Ethyl 4-(methoxyacetamido)cinnamate

HRID 1290209Notes

Reaction equation

HRID 1290209 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH3:15][O:16][CH2:17][C:18](O)=[O:19].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:15][O:16][CH2:17][C:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1)=[O:19]

Participants

7

Reactant 4

HCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 53928658Ethyl 4-(methoxyacetamido)cinnamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-aminocinnamate (2.00 g) and methoxyacetic acid (1.04 ml) in N,N-dimethylformamide (20 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.61 g) and 1-hydroxybenzotriazole (2.12 g) at ambient temperature, and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into water, and extracted with dichloromethane. The organic layer was washed with aqueous sodium bicarbonate solution and water, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give ethyl 4-(methoxyacetamido)cinnamate (2.34 g) as a pale yellow powder.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with aqueous sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-657eecaad26a47b7b1501a3d8022aba3
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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