Cyclopropylamine → HCID 178471877, compound

HRID 637289Notes

Reaction equation

HRID 637289 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[F:5][C:6]1[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[CH:20][C:7]=1[C:8]([C:10](=[CH:16]OCC)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9]>C(O)C>[F:5][C:6]1[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[CH:20][C:7]=1[C:8]([C:10](=[CH:16][NH:4][CH:1]1[CH2:3][CH2:2]1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 54346083Ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

Product 1

HCID 178471877HCID 178471877, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.2 g of cyclopropylamine are added dropwise to a solution of 123.9 g of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (5) in 250 ml of ethanol, while cooling with ice and stirring. When the exothermic reaction has abated, stirring is continued for a further hour at room temperature, the solvent is stripped off in vacuo and the residue is recrystallised from cyclohexane petroleum ether. 115 g of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-cyclopropylamino-acrylate (6) of melting point 63°-65° C. are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customWhen the exothermic reaction
  3. stirringstirring
  4. waitis continued for a further hour at room temperature
  5. customthe residue is recrystallised from cyclohexane petroleum ether

Sources & evidence

ORD record
ord-055a3d41df9a4525b68a1411f52e9783
Source dataset
uspto-grants-1985_12
Patent number
US04556658

Reaction notes

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