Acetic Acid → HCID 68481980, compound

HRID 451335Notes

Reaction equation

HRID 451335 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4]C(OCC)=O.[C:11]([OH:14])(=[O:13])[CH3:12].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23]1(C)C=CC=C[CH:24]=1>C(O)C>[Cl:1][CH2:2][C:3]([NH:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:4][CH2:12][C:11]([O:14][CH2:23][CH3:24])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 7504BenzylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 68481980HCID 68481980, compoundYield 52%

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, 65.7 g of benzylamine 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. 157.8 g of ethyl 4-chloro-3-(benzylamino)but-2-enecarboxylate are obtained in a purity of 50% (this corresponds to 52% 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-649d1013af0046f092331c20e72c0ab9
Source dataset
uspto-grants-2013_07
Patent number
US08487112B2

Reaction notes

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