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

HRID 2198942Notes

Reaction equation

HRID 2198942 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e1e70dad6c274ced90fb0813e14cc5d2
Source dataset
uspto-grants-1982_11
Patent number
US04360530

Reaction notes

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