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

HRID 451020

反応式

HRID 451020 の反応式
[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

参加物

5

反応物 2

HCID 119708Isocyanatocarbonyl chlorideHCID 2901542-Phenylcyclopentanone

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7e48c3538ea046509c1a62350397de1a
出典データセット
uspto-grants-2013_07
特許番号
US08486952B2

関連ノート

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