3-Aminopropionitrile → 2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

HRID 1282444Notes

Reaction equation

HRID 1282444 reaction equation
[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9](O)=[O:10])[C:6]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:5]=2[O:4]1.[C:22]([CH2:24][CH2:25][NH2:26])#[N:23].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:22]([CH2:24][CH2:25][NH:26][C:9]([C:7]1[C:6]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:5]=2[O:4][C:3]([CH2:2][F:1])([CH2:20][F:21])[CH:8]=1)=[O:10])#[N:23]

Participants

5

Reactant 3

HCID 16473-AminopropionitrileHCID 11430Potassium CarbonateHCID 98796402,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid

Product 1

HCID 99507522,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled mixture of 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid (0.20 g) and tetrahydrofuran (3 ml), N,N′-carbonyldiimidazole (0.12 g) was added with stirring and the mixture was stirred for 1 hour. Thereafter, 2-cyanoethylamine (0.06 g) was added and the mixture was stirred first under cooling with ice for 1 hour, then at room temperature for 12 hours. To the reaction mixture, an aqueous solution of potassium carbonate was added, followed by extraction with methylene chloride; the organic layer was washed with water and dried; the solvent was distilled off and the resulting residue was recrystallized with a solvent consisting of a mixture of ethyl acetate and hexane, thereby giving the titled compound (0.20 g) having a melting point of 135-136° C.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 1 hour
  3. stirringthe mixture was stirred first
  4. temperatureunder cooling with ice for 1 hour
  5. extractionfollowed by extraction with methylene chloride
  6. washthe organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customthe resulting residue was recrystallized with a solvent
  10. additionconsisting of a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ae502500cc4e48ab9c937a5d11768ae4
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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