Cyclopropylamine → HCID 178471868, compound

HRID 2291124Notes

Reaction equation

HRID 2291124 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 were added dropwise to a solution of 24.9 g of ethyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-ethoxy-acrylate in 80 ml of ethanol while cooling with ice and stirring. When the exothermic reaction had ceased, the mixture was stirred for another hour at room temperature, the solvent was stripped off in vacuo, and the residue was recrystallised from cyclohexane/petroleum ether. 22.9 g of ethyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-cyclopropylamino-acrylate (R1 =C2H5) of melting point 89° to 90° C. were obtained.

Workup

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

Sources & evidence

ORD record
ord-ebd7fd6ed9f64b83921bd2a38bdb5d27
Source dataset
uspto-grants-1986_10
Patent number
US04620007

Reaction notes

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