Acetic Acid → HCID 86644235, compound

HRID 451333Notes

Reaction equation

HRID 451333 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])[CH:16]([CH3:18])[CH3:17].[C:20]1(C)C=CC=C[CH:21]=1>C(O)C>[Cl:1][CH2:2][C:3]([NH:19][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:4][CH2:12][C:11]([O:14][CH2:20][CH3:21])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 6558IsobutylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 86644235HCID 86644235, compoundYield 86%

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, 47.4 g of isobutylamine 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. 140.8 g of ethyl 4-chloro-3-(isobutylamino)but-2-enecarboxylate are obtained in a purity of 79% (this corresponds to 86% 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-4ded625ff5df4b219b6aa55c5b9ef778
Source dataset
uspto-grants-2013_07
Patent number
US08487112B2

Reaction notes

Loading…