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

HRID 1483029노트

반응식

HRID 1483029 반응식
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]

참가 물질

5

반응물 3

HCID 4873Potassium ChlorideHCID 58012-AminophenolHCID 701982-Chloroacrylonitrile

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bd0f5f84560741e393df1207e8f4711f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416138B2

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