Cyclopropylamine → HCID 178471868, compound

HRID 637943Notes

Reaction equation

HRID 637943 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:23]=[C:22]([Cl:24])[C:21]([F:25])=[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>[Cl:5][C:6]1[CH:23]=[C:22]([Cl:24])[C:21]([F:25])=[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 53427585Ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate

Product 1

HCID 178471868HCID 178471868, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.3 g of cyclopropylamine are added dropwise to a solution of 24.9 g of ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxy-acrylate (5) in 80 ml of ethanol, while cooling with ice and stirring. When the exothermic reaction has subsided, the mixture is stirred for a further hour at room temperature, the solvent is stripped off in vacuo and the residue is recrystallised from cyclohexane/petroleum ether. 22.9 g of ethyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-cyclopropylamino-acrylate (6) of melting point 89° to 90° C. are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customWhen the exothermic reaction
  3. stirringthe mixture is stirred for a further hour at room temperature
  4. customthe residue is recrystallised from cyclohexane/petroleum ether

Sources & evidence

ORD record
ord-28e078a839884b2b88d5dbe3b287ef2d
Source dataset
uspto-grants-1985_12
Patent number
US04559342

Reaction notes

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