Triethylamine → Ethyl 3-oxo-2-[(3-phenylacryloyl)amino]butanoate

HRID 746013Notes

Reaction equation

HRID 746013 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([C:16]([CH3:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:19](Cl)(=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[C:19]([NH:9][CH:10]([C:16]([CH3:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 13282897Ethyl 2-amino-3-oxobutanoate hydrochloride

Product 1

HCID 53679532Ethyl 3-oxo-2-[(3-phenylacryloyl)amino]butanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (8.3 ml) was added dropwise to a solution of ethyl 2-aminoacetoacetate hydrochloride (5.43 g) and cinnamoyl chloride (5.0 g) in chloroform (90 ml) with ice-cooling and stirring. After 20 minutes, the mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was treated with isopropyl ether to give ethyl 2-cinnamoylaminoacetoacetate as crystals; yield 6.1 g (73.9%). Recrystallization from ethanol gave colorless needles melting at 113°-114° C.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. additionthe residue was treated with isopropyl ether

Sources & evidence

ORD record
ord-8efedca953ae43c2bed0b67ab6331cf5
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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