2,4-Difluoroaniline → HCID 13606905, compound

HRID 1163332Notes

Reaction equation

HRID 1163332 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:10](=[O:20])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([Cl:18])=[CH:13][C:12]=1Cl)=[CH:6]OCC)[CH3:2].[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25].[H-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:10](=[O:20])[C:11]2[C:12](=[CH:13][C:14]([Cl:18])=[C:15]([F:17])[CH:16]=2)[N:25]([C:24]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=2[F:22])[CH:6]=1)=[O:21])[CH3:2]

Participants

6

Reactant 3

HCID 97092,4-DifluoroanilineHCID 24758Sodium hydrideHCID 53427585Ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate

Product 1

HCID 13606905HCID 13606905, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2 g 2-(2,4-dichloro-5-fluoro-benzoyl)-3-ethoxy-acrylic acid ethyl ester (5.97 mmol) and 0.6 ml of 2,4-difluoroaniline (5.97 mmol) in 15 ml of ethanol was stirred at reflux for 25 hrs. The reaction was monitored by TLC. The ethanol was evaporated and the residual ethanol was distilled from an azeotrope with 20 ml heptane and 20 ml ethyl acetate. The yellow oil was dissolved in 20 ml of THF, reacted with 315 mg of a 50% NaH suspension in oil (6.56 mmol) and stirred at reflux for 20 hrs. The solution was diluted with ethyl acetate, washed with water and brine, dried over Mg sulfate, filtered and the filtrate evaporated.

Workup

  1. temperatureat reflux for 25 hrs
  2. customThe ethanol was evaporated
  3. distillationthe residual ethanol was distilled from an azeotrope with 20 ml heptane and 20 ml ethyl acetate
  4. dissolutionThe yellow oil was dissolved in 20 ml of THF
  5. temperatureat reflux for 20 hrs
  6. washwashed with water and brine
  7. dry with materialdried over Mg sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated

Sources & evidence

ORD record
ord-82fccc7150b5454ea44a4b1383e1da08
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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