Water → HCID 178471887, compound

HRID 36711Notes

Reaction equation

HRID 36711 reaction equation
[Cl:1][C:2]1[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[C:16]([F:22])[C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:23]1([NH2:26])[CH2:25][CH2:24]1.O>C(O)C>[Cl:1][C:2]1[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[C:16]([F:22])[C:3]=1[C:4]([C:6](=[CH:12][NH:26][CH:23]1[CH2:25][CH2:24]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 69828CyclopropylamineHCID 53750212Ethyl 2-(2,4-dichloro-3,6-difluorobenzoyl)-3-ethoxyacrylate

Product 1

HCID 178471887HCID 178471887, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.6 g of ethyl 2-(2,4-dichloro-3,6-difluorobenzoyl)-3-ethoxy-acrylate are dissolved in 50 ml of ethanol, and 2.75 g of cyclopropylamine are added dropwise, while cooling. The mixture is stirred at room temperature for 1 hour, 50 ml of water are added, while cooling with ice, and the precipitate is filtered off with suction, rinsed with ethanol/H2O (1:1) and dried. 14.1 g of ethyl 2-(2,4-dichloro-3,6-difluorobenzoyl)-3-cyclopropylamino-acrylate of melting point 106°-107° C. are obtained.

Workup

  1. temperaturewhile cooling
  2. temperaturewhile cooling with ice
  3. filtrationthe precipitate is filtered off with suction
  4. washrinsed with ethanol/H2O (1:1)
  5. customdried

Sources & evidence

ORD record
ord-e3136307fcaa404e9a8c23fceb1d7694
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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