Water → 4,5-Diethyloxazol-2-amine
Reaction equation
[CH3:1][CH2:2][C:3](=O)[CH:4]([CH2:6][CH3:7])[OH:5].[N:9]#[C:10][NH2:11].[O-]CC.[Na+].O>C(O)C>[NH2:11][C:10]1[O:5][C:4]([CH2:6][CH3:7])=[C:3]([CH2:2][CH3:1])[N:9]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Propioin (1.03 g, 8.37 mmol) was dissolved in ethanol (15 mL). Cyanamide (0.75 g, 17.7 mmol) and sodium ethoxide (1.21 g, 17.7 mmol) were added, and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (dichloromethane:methanol=9:1) to give the title compound (369.2 mg, 29.7%) as a yellow amorphous.
Workup
- extractionextracted with ethyl acetate
- washAfter the organic layer was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- customthe residue obtained by evaporation under reduced pressure
- customwas purified by chromatography on silica gel (dichloromethane:methanol=9:1)
Sources & evidence
- ORD record
- ord-dc9178b141b9494d9295114ee8c3f8ba
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097759B2
Reaction notes
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