Water → HCID 20517772, compound

HRID 2058530Notes

Reaction equation

HRID 2058530 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.[CH2:12]([N:14]([CH2:23][CH3:24])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1)[CH3:13].O>C1C=CC=CC=1>[CH2:23]([N:14]([CH2:12][CH3:13])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[O:20][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:17][CH:16]=1)[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 671144-(Diethylamino)benzaldehydeHCID 3082152,2-Dimethyl-3-phenyl-2H-azirene

Product 1

HCID 20517772HCID 20517772, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4 g of 2,2-dimethyl-3-phenyl-2H-azirine and 5 g of 4-diethylaminobenzaldehyde were exposed to light in 350 ml of benzene at 230° C. for 4 hours under an atmosphere of argon with a mercury high-pressure lamp of 150 watt in a water-cooled ring-mantle vessel through a 3 mm thick filter of Pyrex glass. After removing the solvent in a water-jet vacuum, the residue was crystallized from n-hexane/acetone and then a second time from n-pentane/acetone. The crystalline product was then dried at 60° C. in the water-jet vacuum, and there were obtained 3,4 g of 5-[p-(diethylamino)-phenyl]-2,2-dimethyl-4-phenyl-3-oxazoline having a melting point of 104°-105° C.

Workup

  1. temperaturecooled ring-mantle vessel through a 3 mm
  2. filtrationthick filter of Pyrex glass
  3. customAfter removing the solvent in a water-jet vacuum
  4. customthe residue was crystallized from n-hexane/acetone
  5. dry with materialThe crystalline product was then dried at 60° C. in the water-jet vacuum

Sources & evidence

ORD record
ord-72ace7f40c604f34b503112905f73560
Source dataset
uspto-grants-1982_03
Patent number
US04317914

Reaction notes

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