Ethyl Acetate → HCID 1807007, compound

HRID 1503240Notes

Reaction equation

HRID 1503240 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[F:11][C:12]([F:21])([F:20])[C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([C:12]([F:11])([F:20])[F:21])=[CH:14][CH:15]=2)=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 99644-(Trifluoromethyl)anilineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 1807007HCID 1807007, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloronicotinoyl chloride (0.83 g) was dissolved in toluene (15 mL), and the solution was cooled to 0° C. 4-(Trifluoromethyl)aniline (1.6 g) was added thereto at 0° C., and the mixture was stirred at room temperature for 10 hours. Ethyl acetate was added thereto, and the organic layer was washed with a 1 N aqueous sodium hydroxide solution and water and dried over sodium sulfate. After concentration under reduced pressure, the obtained solid was collected by filtration and washed with diethyl ether. The solid was dried under reduced pressure to obtain the title compound (0.88 g) as a white solid (yield: 29%).

Workup

  1. washthe organic layer was washed with a 1 N aqueous sodium hydroxide solution and water
  2. dry with materialdried over sodium sulfate
  3. concentrationAfter concentration under reduced pressure
  4. filtrationthe obtained solid was collected by filtration
  5. washwashed with diethyl ether
  6. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-917dd89b158d48439bdeea353b405837
Source dataset
uspto-grants-2015_12
Patent number
US09212170B2

Reaction notes

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