Benzenamine, 2-chloro-4-fluoro- → HCID 178471927, compound

HRID 1415918Notes

Reaction equation

HRID 1415918 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:10][C:11]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:12]=1[C:13]([C:15](=[CH:21]OCC)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14]>C(Cl)(Cl)Cl>[F:10][C:11]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:12]=1[C:13]([C:15](=[CH:21][NH:4][C:3]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[Cl:1])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14]

Participants

4

Reactant 2

HCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 54008204Ethyl 3-(2,4,5-trifluorophenyl)-3-oxo-2-(ethoxymethylene)propanoate

Product 1

HCID 178471927HCID 178471927, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

With ice cooling, 5 ml of a chloroform solution containing 1.2 ml of 2-chloro-4-fluoroaniline was added dropwise to 13 ml of a chloroform solution containing 2.46 g of ethyl 2-(2,4,5-trifluorobenzoyl)-3-ethoxyacrylate and stirred overnight at room temperature. The solvent was distilled off then to the residue, ethanol was added. The resulting crystals were collected by filtration and washed with diethyl ether, to give ethyl 2-(2,4,5-trifluorobenzoyl)-3-(2-chloro-4-fluorophenylamino)acrylate. To 15 ml of a N,N-dimethylformamide solution containing 3.00 g of ethyl 2-(2,4,5-trifluorobenzoyl)-3-(2-chloro-4-fluorophenylamino)acrylate was added 1.03 g of potassium carbonate. The solution was stirred for 90 minutes at room temperature. The reaction solution was poured into ice water, the precipitated solid was collected by filtration and washed with ethanol and diethyl ether, to give 2.74 g of the title compound.

Workup

  1. distillationThe solvent was distilled off
  2. additionto the residue, ethanol was added
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-52787acfb65f48819a1e3b50186df657
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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