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

HRID 2198938Notes

Reaction equation

HRID 2198938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH3:12])([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=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>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:19]([C:18]3[CH:21]=[CH:22][C:15]([N:14]([CH3:23])[CH3:13])=[CH:16][CH:17]=3)[O:20][C:9]([CH3:11])([CH3:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 126213493-(3-Chlorophenyl)-2,2-dimethyl-2H-azirene

Product 1

HCID 30614374-[4-(3-Chlorophenyl)-2,2-dimethyl-2,5-dihydro-1,3-oxazol-5-yl]-N,N-dimethylaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3 g of 3-(m-chlorophenyl)-2,2-dimethyl-2H-azirine and 2.4 g of p-(dimethylamino)benzaldehyde were exposed to light for 2 hours in 350 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 twice on aluminum oxide (neutral, activity 1), the elution was carried out in both cases with n-hexane/ether (9:1). Crystallization from n-hexane gave 4-(m-chlorophenyl)-5-[p-(dimethylamino)phenyl]-2,2-dimethyl-3-oxazoline which melted at 96°-97° C. after drying for 5 hours at 60° C. and 13 Torr.

Workup

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

Sources & evidence

ORD record
ord-cbc1ac71019f4bc588f872abceae425d
Source dataset
uspto-grants-1982_11
Patent number
US04360530

Reaction notes

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