Triethylamine → Ethyl 4-propionamidocinnamate

HRID 564916Notes

Reaction equation

HRID 564916 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.C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>ClCCl.CN(C)C(N)CC>[C:22]([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:25])[CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 97826Ethyl 3-(4-aminophenyl)acrylate

Product 1

HCID 54078953Ethyl 4-propionamidocinnamateYield 87.9%

Reagents, catalysts & solvents 2

HCID 169191N,N-DimethylpropanediamineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of ethyl 4-aminocinnamate (300 mg), triethylamine (167 mg) and dichloromethane (3 ml) was added a solution of propionyl chloride (182 mg) in dichloromethane (1 ml) in an ice-water bath, and the mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added 4 drops of N,N-dimethyl-propanediamine, and the mixture was further stirred for 5 minutes. The reaction mixture was washed with water, dried over magnesium sulfate, and evaporated in vacua. The residue was crystallized from diisopropyl ether to give ethyl 4-propionamidocinnamate (341 mg) as a colorless powder.

Workup

  1. stirringthe mixture was further stirred for 5 minutes
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacua
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-1dd8c798b67c45feaf786c377a2ae41e
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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