2-Phenylcyclohexanone → 4a-phenyl-4a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione

HRID 451124

反応式

HRID 451124 の反応式
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)([N:16]=[C:17]=[O:18])=[O:15]>C(OCC)(=O)C>[C:1]1([CH:7]2[C:8]3[O:13][C:17](=[O:18])[NH:16][C:14](=[O:15])[C:9]=3[CH2:10][CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]23[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]2[O:13][C:17](=[O:18])[NH:16][C:14]3=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 955922-PhenylcyclohexanoneHCID 119708Isocyanatocarbonyl chloride

生成物 2

HCID 105143688-phenyl-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione収率 19.62%HCID 105381824a-phenyl-4a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione収率 35.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

A solution of 2-phenylcyclohexanone (1.500 g, 8.61 mmol) and carbonisocyanatidic chloride (0.966 mL, 12 mmol) was stirred at 58° C. in a high-pressure vessel (75 mL) for 1 h. The temperature was raised to 130° C. and the reaction mixture was stirred for 2 h. After cooling to room temperature, the reaction mixture solidified. The solid residue was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuum and the oily residue was purified by column chromatography on silica gel to provide 8-phenyl-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (415.0 mg, 1.689 mmol, 19.62% yield) as white solid and 4a-phenyl-4a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (746.4 mg, 3.04 mmol, 35.3% yield) as white solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated aqueous solution of sodium bicarbonate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuum
  8. customthe oily residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-ece7c552872f43cb8632bcaa31b47b50
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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