Urea → 4,4,8-Trimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one
Reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].N[C:14](N)=[O:15]>C(OCC)C>[CH3:11][C:9]1([CH3:10])[O:12][C:14](=[O:15])[NH:1][C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 2.88 g of 2-(2-amino-3-methylphenyl)propan-2-ol and 2.14 g of urea is stirred in a sealed vessel at 150° C. over 6 hours. The reaction mixture is cooled to room temperature, admixed with diethyl ether, clarified by filtration and concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.22 (1:2 EtOAc-heptane); Rt=3.46.
Workup
- temperatureThe reaction mixture is cooled to room temperature
- filtrationclarified by filtration
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-9c2f244c5442490280210d531520598e
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842688B2
Reaction notes
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