Triethylamine → 2-(4,5-Dichloro-imidazol-2-yl)-5-phenoxy-1,3,4-oxadiazole

HRID 1164376노트

반응식

HRID 1164376 반응식
[C:1]1([O:7][C:8](=[O:11])[NH:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[N:14]=[C:15]([C:19](Cl)(Cl)Cl)[NH:16][C:17]=1[Cl:18].C(N(CC)CC)C>O1CCOCC1>[Cl:12][C:13]1[N:14]=[C:15]([C:19]2[O:11][C:8]([O:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:9][N:10]=2)[NH:16][C:17]=1[Cl:18]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 134791Hydrazinecarboxylic acid, phenyl esterHCID 124825734,5-Dichloro-2-(trichloromethyl)-1H-imidazole

생성물 1

HCID 1357554452-(4,5-Dichloro-imidazol-2-yl)-5-phenoxy-1,3,4-oxadiazole수율 72.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

16.7 g (0.11 mol) of carbazic acid phenyl ester were added in portions, at room temperature, to a solution of 25.4 g (0.1 mol) of 4,5-dichloro-2-trichloromethyl-imidazole in 200 ml of dioxane. After the slightly exothermic reaction had subsided, the mixture was gradually warmed to the boil and boiled for a further 2 hours under reflux. It was then cooled to room temperature and 20.2 g (0.2 mol) of triethylamine were added dropwise. The mixture was stirred for a further 2 hours at 50° C., the insoluble constituents were filtered off and the filtrate was evaporated in vacuo. The residue was treated with water and the product was filtered off, washed with water and dried. 21.5 g (72.5% of theory) of 2-(4,5-dichloro-imidazol-2-yl)-5-phenoxy-1,3,4-oxadiazole were obtained. Melting point: 109° C. (from toluene).

후처리

  1. customAfter the slightly exothermic reaction
  2. temperaturethe mixture was gradually warmed to the boil
  3. temperatureunder reflux
  4. filtrationthe insoluble constituents were filtered off
  5. customthe filtrate was evaporated in vacuo
  6. additionThe residue was treated with water
  7. filtrationthe product was filtered off
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-d7276870b2c145e1877af41999adc4fd
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04369186

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