Phosgene → 3-(2-chloro-5-nitrophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

HRID 1165927노트

반응식

HRID 1165927 반응식
[C:1](Cl)(Cl)=[O:2].C(Cl)(=O)OC(Cl)(Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[NH:23][NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[N:23]1[N:24]=[C:25]([C:26]([CH3:27])([CH3:29])[CH3:28])[O:30][C:1]1=[O:2]

참가 물질

5

반응물 3

HCID 6371PhosgeneHCID 10426DiphosgeneHCID 142806541-(2-Chloro-5-nitrophenyl)-2-(2,2-dimethylpropionyl)hydrazine

생성물 1

HCID 142806563-(2-chloro-5-nitrophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A toluene solution of phosgene prepared by adding active carbon and toluene (500 ml) to trichloromethyl chlorocarbonate (82.5 g) was added to 1-(2-chloro-5-nitrophenyl) -2-(2,2-dimethylpropionyl)hydrazine (42.23 g), and the resultant mixture was heated under reflux for 2 hours. Active carbon was further added thereto, and heating under reflux was continued for 15 hours. After removal of active carbon by filtration, the filtrate was concentrated. To the concentrated solution, a solution of triethylamine (23.54 g) in toluene (155 ml) was added, and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was combined with water. The toluene layer was separated, washed with water, dried and concentrated under reduced pressure to give 3-(2-chloro-5-nitrophenyl)-5-(1,1-dimethylethyl) -1,3,4-oxadiazol-2(3H)-one (47.51 g). m.p., 130.4° C..

후처리

  1. temperatureunder reflux for 2 hours
  2. additionActive carbon was further added
  3. temperatureheating
  4. temperatureunder reflux
  5. customAfter removal of active carbon
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. additionTo the concentrated solution, a solution of triethylamine (23.54 g) in toluene (155 ml) was added
  9. customThe toluene layer was separated
  10. washwashed with water
  11. customdried
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5c1eba058b5d4badad289d0b300f071a
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04912225

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