4-(Dimethylamino)Benzaldehyde → 4-[2,2-Dimethyl-4-(2-methylphenyl)-2,5-dihydro-1,3-oxazol-5-yl]-N,N-dimethylaniline

HRID 2058535Notes

Reaction equation

HRID 2058535 reaction equation
[CH3:1][C:2]1([CH3:12])[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:11])=[N:3]1.[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>O1CCOCC1>[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[O:20][C:2]([CH3:1])([CH3:12])[N:3]=[C:4]2[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:11])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 20517775HCID 20517775, compound

Product 1

HCID 30614384-[2,2-Dimethyl-4-(2-methylphenyl)-2,5-dihydro-1,3-oxazol-5-yl]-N,N-dimethylaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.3 g of 2,2-dimethyl-3-(o-tolyl)-2H-azirine and 2.5 g of p-(dimethylamino)benzaldehyde were exposed to light for 2 hours in 290 ml of 1,4-dioxane (with the light source described in Example 2). After removing the solvent in a water-jet vacuum, the residue was chromatographed on aluminum oxide (neutral, activity 1), the elution was carried out with n-heptane/ether (9:1). Crystallization from ethanol/water gave 5-[p-(dimethylamino)phenyl]-2,2-dimethyl-4-(o-tolyl)-3-oxazoline which melted at 89°-90° C. after drying for 16 hours at 30° C. and 13 Torr.

Workup

  1. customAfter removing the solvent in a water-jet vacuum
  2. customthe residue was chromatographed on aluminum oxide (neutral, activity 1)
  3. washthe elution
  4. customCrystallization from ethanol/water

Sources & evidence

ORD record
ord-52c3b77c8b8844de997815b60719228a
Source dataset
uspto-grants-1982_03
Patent number
US04317914

Reaction notes

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