Cyclopropylamine → HCID 178471868, compound

HRID 652055Notes

Reaction equation

HRID 652055 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-59655440d0a948e8920e5b631529a89f
Source dataset
uspto-grants-1987_06
Patent number
US04670444

Reaction notes

Loading…