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

HRID 1164376ノート

反応式

HRID 1164376 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d7276870b2c145e1877af41999adc4fd
出典データセット
uspto-grants-1983_01
特許番号
US04369186

反応ノート

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