Potassium Chloride → 3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile

HRID 1483029ノート

反応式

HRID 1483029 の反応式
Cl[C:2](=[CH2:5])[C:3]#[N:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[Cl-].[K+]>CC(C)=O>[O:13]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH2:5][CH:2]1[C:3]#[N:4]

参加物

5

反応物 3

HCID 4873Potassium ChlorideHCID 58012-AminophenolHCID 701982-Chloroacrylonitrile

生成物 1

HCID 27955043,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile収率 31.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Combine 2-chloro-2-propenenitrile (3.0 g, 34.3 mmol), 2-aminophenol (3.27 g, 29.96 mmol), acetone (50 mL), and potassium chloride (5 g, 36.18 mmol). Stir the mixture at ambient temperature for 16 hours. Filter the mixture and wash the filter cake with EtOAc. Concentrate the filtrate under reduced pressure to give a residue. Purify via flash column chromatography using a gradient of 1-50% EtOAc in petroleum ether to elute. Combine the product fractions and remove solvents under reduced pressure to provide the title compound (1.5 g, 21.6%). MS (m/z): 161 (M+1).

後処理

  1. filtrationFilter the mixture
  2. washwash the filter cake with EtOAc
  3. concentrationConcentrate the filtrate under reduced pressure
  4. customto give a residue
  5. customPurify via flash column chromatography
  6. washto elute
  7. customCombine the product fractions and remove solvents under reduced pressure

出典と根拠

ORDレコード
ord-bd0f5f84560741e393df1207e8f4711f
出典データセット
uspto-grants-2016_08
特許番号
US09416138B2

反応ノート

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