Phosgene → 5-(9H-fluoren-9-ylmethoxy)-3H-1,3,4-oxadiazol-2-one

HRID 1828769ノート

反応式

HRID 1828769 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][NH2:19])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:20]([O-])(O)=[O:21].[Na+].C(Cl)(Cl)=O>C(Cl)Cl.O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]3[O:17][C:20](=[O:21])[NH:19][N:18]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 6371PhosgeneHCID 1618839-Fluorenylmethyl carbazateHCID 516892Sodium Bicarbonate

生成物 1

HCID 107551765-(9H-fluoren-9-ylmethoxy)-3H-1,3,4-oxadiazol-2-one収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of N-[(9H-fluoren-9-ylmethoxy)carbonyl]hydrazine (141) (1.49 g, 5.78 mmol), CH2Cl2 (60 ml) and saturated NaHCO3 solution (60 ml) was stirred vigorously at 0° C. for 5 minutes, and the solution was then left for 5 minutes without stirring. Phosgene (1.89 M in toluene, 7.95 ml, 15.0 mmol) was then carefully added to the lower, organic phase using a syringe, and stirring of the reaction mixture was begun again immediately after the addition. After 10 minutes, water (20 ml) and CH2Cl2 (20 ml) were added to the reaction mixture. The phases were then separated rapidly, the aqueous phase was extracted with CH2Cl2 (50 ml), and the combined organic phases were dried over Na2SO4. Removal of the solvent under reduced pressure and drying gave a colourless solid (1.35 g, 4.82 mmol, 83%).

後処理

  1. waitthe solution was then left for 5 minutes
  2. stirringwithout stirring
  3. stirringstirring of the reaction mixture
  4. additionafter the addition
  5. waitAfter 10 minutes
  6. customThe phases were then separated rapidly
  7. extractionthe aqueous phase was extracted with CH2Cl2 (50 ml)
  8. dry with materialthe combined organic phases were dried over Na2SO4
  9. customRemoval of the solvent under reduced pressure
  10. customdrying

出典と根拠

ORDレコード
ord-726240ce1d7c4e2f8de4cc0882c90c2a
出典データセット
uspto-grants-2006_06
特許番号
US07060707B2

反応ノート

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