Water → HCID 178471933, compound

HRID 345839

Reaction equation

HRID 345839 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(O[CH:13]=[C:14]([C:20](=[O:32])[C:21]1[C:26]([F:27])=[C:25]([F:28])[C:24]([F:29])=[C:23]([F:30])[C:22]=1[F:31])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.O>C(O)C>[F:27][C:26]1[C:25]([F:28])=[C:24]([F:29])[C:23]([F:30])=[C:22]([F:31])[C:21]=1[C:20]([C:14](=[CH:13][NH:4][C:3]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[F:1])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 97092,4-DifluoroanilineHCID 53952225Ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)-acrylate

Product 1

HCID 178471933HCID 178471933, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

44.3 g of 2,4-difluoroaniline are added dropwise to a solution of 115 g of ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)-acrylate in 380 ml of ethanol, while cooling with ice and stirring. The mixture is stirred at room temperature for 1 hour, 380 ml of water are added, while cooling with ice, and the precipitate is filtered off with suction, washed with ethanol/H2O (1:1) and dried. 135.4 g of the title compound of melting point 97°-99° C. are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. temperaturewhile cooling with ice
  4. filtrationthe precipitate is filtered off with suction
  5. washwashed with ethanol/H2O (1:1)
  6. customdried

Sources & evidence

ORD record
ord-778ffdc1a0364023b5c95adefd9bafaf
Source dataset
uspto-grants-1991_10
Patent number
US05059597

Linked notes

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