Pyridine → 4-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-3-methylbenzamide

HRID 587838Notes

Reaction equation

HRID 587838 reaction equation
[CH2:1]([C:3]1[CH:9]=[C:8]([C:10]([F:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]([CH3:20])[C:4]=1[NH2:5])[CH3:2].N1C=CC=CC=1.[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][C:30]=1[CH3:38])#[N:28]>O1CCCC1.CN(C)C1C=CN=CC=1.O>[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:5][C:4]2[C:6]([CH3:20])=[CH:7][C:8]([C:10]([F:19])([C:11]([F:14])([F:13])[F:12])[C:15]([F:16])([F:17])[F:18])=[CH:9][C:3]=2[CH2:1][CH3:2])=[O:34])=[CH:31][C:30]=1[CH3:38])#[N:28]

Participants

7

Reactant 3

HCID 1049PyridineHCID 227346102-Methyl-6-ethyl-4-(heptafluoro-prop-2-yl)-anilineHCID 866666194-Cyano-3-methylbenzoyl chloride

Product 1

HCID 866666204-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-3-methylbenzamideYield 84.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2-Ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylaniline (1.7 g) and pyridine (0.88 g) were dissolved in tetrahydrofuran (30 ml). To the solution, the crude product of 4-cyano-3-methylbenzoyl chloride (1.0 g) and 4-dimethylaminopyridine (0.03 g) were added and the mixture was stirred under heating at 50° C. for 2 hours. After adjusting to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with 2N hydrochloric acid and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with a mixed solvent of hexane and ethyl acetate (ethyl acetate 10%) to obtain 4-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-3-methylbenzamide (2.1 g, yield 83%).

Workup

  1. customAfter adjusting to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with 2N hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering off the drying agent
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. washThe crude product was washed with a mixed solvent of hexane and ethyl acetate (ethyl acetate 10%)

Sources & evidence

ORD record
ord-575f2f917f1f4024b549cdea09678fd8
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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