Hydrochloric Acid → 5-Ethyl-1,3-benzoxazol-2(3H)-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].N[C:12](N)=[O:13].Cl>>[CH2:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:10][C:12](=[O:13])[NH:1][C:2]=2[CH:7]=1)[CH3:9]Participants
4
Conditions
- Temperature
- 180 °C
Procedure
8.2 g (0.06 M) 2-amino-4-ethylphenol and 5.4 g (0.09 M) urea were thoroughly mixed and heated in an oil bath to 180° C. for 2.0 hours. Thereafter the mixture was allowed to cool to 100° C. HCl solution (1.0 normal) was added to the mixture while stirring and the mixture was cooled to room temperature. The cooled mixture was extracted three times with methylene chloride. The combined organic phases were dried and stripped in vacuum. The sample yielded 5.9 g dark solid with a melting point of 75°-77° C. Spectroscopic data: nuclear magnetic resonance (NMR), C-13 NMR, infrared, and mass spectroscopy are consistent with the proposed structure.
Workup
- temperatureto cool to 100° C
- temperaturethe mixture was cooled to room temperature
- extractionThe cooled mixture was extracted three times with methylene chloride
- customThe combined organic phases were dried
Sources & evidence
- ORD record
- ord-67e13d2a0c1e4ccaae63f5a85b478ea4
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05232899
Reaction notes
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