Acetic Acid → HCID 86644238, compound

HRID 451337Notes

Reaction equation

HRID 451337 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4]C(OCC)=O.[C:11]([OH:14])(=[O:13])[CH3:12].[F:15][CH:16]([F:19])[CH2:17][NH2:18].[C:20]1(C)C=CC=C[CH:21]=1>C(O)C>[Cl:1][CH2:2][C:3]([NH:18][CH2:17][CH:16]([F:19])[F:15])=[CH:4][CH2:12][C:11]([O:14][CH2:20][CH3:21])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 69484Ethyl 4-chloroacetoacetateHCID 1362742,2-Difluoroethanamine

Product 1

HCID 86644238HCID 86644238, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 197.2 g of ethyl 4-chloroacetoacetate in 1080 ml of toluene are added 13.3 ml of acetic acid. At 10° C.-30° C., with cooling, 100 g of 2,2-difluoroethylamine dissolved in 360 ml of ethanol 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. 278 g of ethyl 4-chloro-3-(2,2-difluoroethylamino)but-2-enecarboxylate are obtained in a purity of 93% (this corresponds to 98% yield).

Workup

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

Sources & evidence

ORD record
ord-edd077b62c064a4c94acad7627430e41
Source dataset
uspto-grants-2013_07
Patent number
US08487112B2

Reaction notes

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