Sodium Cyanide → 2-(Dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile

HRID 1397399ノート

反応式

HRID 1397399 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]=O)[N:12]=2)=[CH:4][CH:3]=1.Cl.[CH3:16][NH:17][CH3:18].[C-:19]#[N:20].[Na+]>C1COCC1.CO.O>[CH3:16][N:17]([CH3:18])[CH:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH:10]=1)[C:19]#[N:20]

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

生成物 1

HCID 673252862-(Dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

2-(4-Fluorophenyl)oxazole-4-carbaldehyde (1.0 g, 5.23 mmol) was dissolved in THF-MeOH (20 mL, 1:1 v/v). This solution was added to a solution of dimethylamine hydrochloride (470 mg, 5.7 mmol) and NaCN (640 mg, 13.0 mmol) in water. The resulting reaction mixture was stirred at room temperature for 2 h, and then diluted with water and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile (1.0 g, crude) as a brown oil, which was used without further purification. MS (ESI) m/z: Calculated for C13H12FN3O: 245.10. found: 245.9 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-01d021e1c29c4e0287e929b2644bd438
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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