4-Amino-2-(trifluoromethyl)benzonitrile → HCID 11246104, compound

HRID 982665Notes

Reaction equation

HRID 982665 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:8](=[O:14])O[C:10](=[O:13])[C:11]=1[CH3:12].[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:8](=[O:14])[N:15]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:17]=2)[C:10](=[O:13])[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 113789433-(5-Chloropentyl)-4-methyl-2,5-furandione

Product 1

HCID 11246104HCID 11246104, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9.46 g of 3-(5-chloropentyl)-4-methyl-2,5-furandione and 8.13 g of 4-amino-2-(trifluoromethyl)benzonitrile in 22 ml of ethanol was mixed under a nitrogen atmosphere with 2.5 g of an activated molecular sieve (0.3 nm), and it was stirred for 2 days at 90° C. For working-up, the molecular sieve was filtered off after cooling, washed with ethanol, and the combined ethanol solutions were concentrated by evaporation. The residue was taken up in ethyl acetate and washed with water as well as saturated sodium chloride solution. After drying on sodium sulfate and concentration by evaporation, it was chromatographed on silica gel with ethyl acetate/hexane/toluene, and 11.69 g of the title compound was thus obtained as a white solid.

Workup

  1. additionwas mixed under a nitrogen atmosphere with 2.5 g of an activated molecular sieve (0.3 nm), and it
  2. filtrationthe molecular sieve was filtered off
  3. temperatureafter cooling
  4. washwashed with ethanol
  5. concentrationthe combined ethanol solutions were concentrated by evaporation
  6. washwashed with water as well as saturated sodium chloride solution
  7. customAfter drying on sodium sulfate and concentration by evaporation, it
  8. customwas chromatographed on silica gel with ethyl acetate/hexane/toluene, and 11.69 g of the title compound
  9. customwas thus obtained as a white solid

Sources & evidence

ORD record
ord-4a049e2a72a5434eb0e8de77a4fe005e
Source dataset
uspto-grants-2005_03
Patent number
US06861432B2

Reaction notes

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