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Reaction id: 0601011031_01, verified by Personal Chemistry ©
NaHSO3
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5a
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water
EtOH
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6a
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Yield: 92% Time: 1800s Temperature: 165 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 7631-90-5 |
104.059 |
1.000 |
2.000 |
208.118 mg |
| Substrate 1 |
176.215 |
1.000 |
1.000 |
176.215 µl |
| EtOH |
46.069 |
0.810 |
8.791 |
500.000 µl |
| water |
18.015 |
1.000 |
27.755 |
500.000 µl |
| Product 1 |
258.292 |
1.000 |
0.000 |
0.000 µl |
Keywords
Addition, Michael Addition, Sulfonation
Comments
Synthesis: This reaction type was developed as one step in a method for synthesis of isothiazolidinone phosphotyrosine mimetics. The subsequent ring closure to form the isothiazolidinone was carried out at room temperature. During optimisation, it was found that the same yields could be obtained by heating the sample to 180°C for 10 minutes, but since that gave higher pressures in the reaction vial, it was decided to carry out the reaction at 165°C. 10 ml reaction vials were used.
The reaction was also scaled up to 3 mmol and carried out in 20 ml vials. This reaction gave similar yields to this scale after crystallisation.
Work-up and purification: After heating, the reaction mixture was filtered and the product then purified by preparative LCMS.
Characterisation: By LCMS and 1H NMR.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Crawley, M. L.; McLaughlin, E.; Zhu, W.; Combs, A. P. Org. Lett. 2005, 7, 5067-5069
Analysis
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