Isocyanatocarbonyl chloride → 7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

HRID 451020

반응식

HRID 451020 반응식
[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](=[O:18])=[N:14][C:15](Cl)=[O:16]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:1]1([CH:7]2[C:8]3[O:12][C:15](=[O:16])[NH:14][C:13](=[O:18])[C:9]=3[CH2:10][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 119708Isocyanatocarbonyl chlorideHCID 2901542-Phenylcyclopentanone

생성물 1

HCID 105373627-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione수율 13.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of 2-phenylcyclopentanone (19.995 g, 125 mmol) and N-(chlorocarbonyl)isocyanate (23.70 g, 225 mmol) was stirred at 58° C. for 1 h and at 130° C. for 45 min. The resulting tarrified reaction mixture was dissolved in ethyl acetate and neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The product was purified by column chromatography on silica gel to give 7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (3.751 g, 16.36 mmol, 13% yield) as brownish solid. LC-MS (M+H)+=230.0. 1H NMR (500 MHz, CDCl3) δ ppm 8.34 (1H, br s), 7.35 (2H, t, J=7.3 Hz), 7.27-7.32 (1H, m), 7.18 (2H, d, J=7.3 Hz), 4.20 (1H, t, J=7.6 Hz), 2.82-2.91 (1H, m), 2.61-2.79 (2H, m), 2.11-2.21 (1H, m).

후처리

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. customThe product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-7e48c3538ea046509c1a62350397de1a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486952B2

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