N-[4-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)phenyl]-N-methylformamide → 4-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)-N-methylaniline
Reaction equation
[CH3:1][C:2]1([CH3:23])[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]([C:13]2[CH:22]=[CH:21][C:16]([N:17](C)[CH:18]=O)=[CH:15][CH:14]=2)[O:3]1>C(O)C>[CH3:18][NH:17][C:16]1[CH:15]=[CH:14][C:13]([CH:4]2[O:3][C:2]([CH3:23])([CH3:1])[N:6]=[C:5]2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:22][CH:21]=1Participants
Procedure
5 g of 4'-(2,2-dimethyl-4-phenyl-3-oxazoline-5-yl)-N-methylformanilide were exposed to light in 2 liters of ethanol under an atmosphere of argon for 8 hours in the apparatus described in Example 4. After evaporation of the solvent in a water-jet vacuum, there remained behind an oil which was chromatographed on silica gel. The elution was carried out with dichloromethane/acetone (95:5). In order to remove accompanying impurities, the product isolated in the foregoing manner was suspended in hot petroleum ether (boiling range 80°-110° C.), removed by filtration under suction and washed on the suction filter with petroleum ether. After drying at 60° C. in a water-jet vacuum, there were obtained 2.5 g of 5-[p-(methylamino)phenyl]-2,2-dimethyl-4-phenyl-3-oxazoline having a melting point of 138°-139° C.
Workup
- customAfter evaporation of the solvent in a water-jet vacuum
- customwas chromatographed on silica gel
- washThe elution
- customIn order to remove
- customthe product isolated in the foregoing manner
- customremoved by filtration under suction
- washwashed on the suction
- filtrationfilter with petroleum ether
- dry with materialAfter drying at 60° C. in a water-jet vacuum
Sources & evidence
- ORD record
- ord-2830e3123fb646ce89756b39a8c6d136
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04317914
Reaction notes
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