Acetic Acid → HCID 86644234, compound

HRID 451332Notes

Reaction equation

HRID 451332 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4]C(OCC)=O.[C:11]([OH:14])(=[O:13])[CH3:12].[CH2:15]([NH2:19])[CH2:16][CH2:17][CH3:18].[C:20]1(C)C=CC=C[CH:21]=1>C(O)C>[Cl:1][CH2:2][C:3]([NH:19][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:4][CH2:12][C:11]([O:14][CH2:20][CH3:21])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 8007ButylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 86644234HCID 86644234, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100 g of ethyl 4-chloroacetoacetate in 300 ml of toluene and 100 ml of ethanol are added 6.7 ml of acetic acid. At 10° C.-30° C., with cooling, 48.3 g of n-butylamine are added dropwise. Subsequently, the mixture is stirred at room temperature for 8 h and the solvent is removed under reduced pressure at temperatures of down to 35° C. 136.6 g of ethyl 4-chloro-3-(n-butylamino)but-2-enecarboxylate are obtained in a purity of 89% (this corresponds to 94% yield).

Workup

  1. temperatureAt 10° C.-30° C., with cooling
  2. customthe solvent is removed under reduced pressure at temperatures of down to 35° C

Sources & evidence

ORD record
ord-cbe449eabd7044a3964d2a6eace94e70
Source dataset
uspto-grants-2013_07
Patent number
US08487112B2

Reaction notes

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