4-Aminobenzaldehyde → 4-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)aniline

HRID 2058538노트

반응식

HRID 2058538 반응식
[CH3:1][C:2]1([CH3:11])[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:3]1.[NH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[BH4-].[Na+]>O1CCOCC1.C(O)C.O>[NH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[O:18][C:2]([CH3:1])([CH3:11])[N:3]=[C:4]2[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:15][CH:14]=1

참가 물질

7

반응물 3

HCID 111584-AminobenzaldehydeHCID 3082152,2-Dimethyl-3-phenyl-2H-azireneHCID 4311764Sodium borohydride

생성물 1

HCID 30614414-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)aniline

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

48 g of 2,2-dimethyl-3-phenyl-2H-azirine and 18.5 g of p-aminobenzaldehyde were exposed to light for 2 hours in 6 liters of 1,4-dioxane in the manner described in Example 1. The solvent was then removed in a water-jet vacuum and the oily residue was chromatographed on silica gel, the elution was carried out with dichloromethane. The thus-obtained crude product (60 g) was stirred in ethanol for 2 hours at room temperature together with 1.8 g of sodium borohydride. The mixture was then diluted with water and extracted with dichloromethane. The crude product obtained after drying and evaporation of the organic phase was purified by pressure chromatography (6 bar) on silica gel with dichloromethane/ether (3:1), whereby there was obtained a product which, after 2-fold recrystallization from ethanol, yielded 5-(p-aminophenyl)-2,2-dimethyl-4-phenyl-3-oxazoline having a melting point of 162°-163° C. after drying for 4 hours 90° C. and 13 Torr.

후처리

  1. customThe solvent was then removed in a water-jet vacuum
  2. customthe oily residue was chromatographed on silica gel
  3. washthe elution
  4. customThe thus-obtained crude product (60 g)
  5. extractionextracted with dichloromethane
  6. customThe crude product obtained
  7. customafter drying
  8. customevaporation of the organic phase
  9. customwas purified by pressure chromatography (6 bar) on silica gel with dichloromethane/ether (3:1)
  10. customwhereby there was obtained a product which
  11. customafter 2-fold recrystallization from ethanol

출처 및 근거

ORD 기록
ord-2442576525d94ad39d37061155a36782
출처 데이터셋
uspto-grants-1982_03
특허 번호
US04317914

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