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

HRID 1828769노트

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HRID 1828769 반응식
[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

참가 물질

6

반응물 3

HCID 6371PhosgeneHCID 1618839-Fluorenylmethyl carbazateHCID 516892Sodium Bicarbonate

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-726240ce1d7c4e2f8de4cc0882c90c2a
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060707B2

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