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

HRID 1282419
ノート
印刷プレビュー

反応式

HRID 1282419 の反応式
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:18][F:19])([CH2:16][F:17])[CH:3]=1.[C:20]([CH2:22][CH2:23][NH2:24])#[N:21].[I-].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.CN(C)[C:49](=[O:51])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]([CH2:22][CH2:23][NH:24][C:49]([C:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:18][F:19])([CH2:16][F:17])[CH:3]=1)=[O:51])#[N:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 16473-AminopropionitrileHCID 4875Potassium IodideHCID 11776TriphenylphosphineHCID 31374DimethylacetamideHCID 184244094-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran

生成物 1

HCID 9950752
2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran (1.73 g), 2-cyanoethylamine (1.44 g), potassium iodide (0.86 g), triphenylphosphine (26 mg), palladium acetate (11 mg) and N,N-dimethylacetamide (10 ml) was stirred under a CO atmosphere at 100° C. for 3 hours. To the reaction mixture, 2 N HCl was added and the precipitating crystals were recovered by filtration. To the recovered crystals, ethyl acetate was added and the insoluble matter was filtered off; the filtrate was washed with a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was recrystallized with an ethanol/water mixed solvent, thereby giving N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide (1.46 g) having a melting point of 129-131° C.

後処理

  1. filtrationthe precipitating crystals were recovered by filtration
  2. additionTo the recovered crystals, ethyl acetate was added
  3. filtrationthe insoluble matter was filtered off
  4. washthe filtrate was washed with a saturated aqueous solution of sodium thiosulfate
  5. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was recrystallized with an ethanol/water mixed solvent

出典と根拠

ORDレコード
ord-b202dfddb9ef489a88d2ce1bb8e10769
出典データセット
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06455708B1

反応ノート

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