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Reaction id: 0501011089_09, verified by Personal Chemistry ©
1c
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2-Chlorobenzylamine
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Acetic acid
MeCN
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3i
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Yield: 97% Time: 600s Temperature: 160 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 |
218.216 |
1.000 |
0.520 |
113.472 µl |
| 89-97-4 |
141.601 |
1.170 |
0.620 |
75.036 µl |
| MeCN |
41.053 |
0.780 |
38.000 |
2000.000 µl |
| Acetic acid |
60.052 |
1.050 |
10.491 |
600.000 µl |
| Product 1 |
314.732 |
1.000 |
0.000 |
0.000 µl |
Keywords
Cyclisation, Heterocyclic, Heterocyclisation, Ring closure, Ring formation
Comments
Synthesis: This method of synthesising heterocycles can be used for a number of substrates, giving 4-aminoquinazolines as well as thieno[3,2-d]pyrimidin-4-ylamine derivatives.
Work-up and purification: After the reaction, the mixture was poured onto a cartridge containing 12 g of Hydromatrix pretreated with NaHCO3 (sat). The solution was eluted directly onto a cartridge with 4 g dry Hydromatrix and 10 g silica. The cartridges were eluted with 5*20 ml ethyl acetate. Evaporation under reduced pressure gave the pure product.
Characterisation: By 1H NMR, 13C NMR, HPLC, HRMS and mp.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Yoon, D. S.; Han, Y.; Stark, T. M.; Haber, J. C.; Gregg, B. T.; Stankovich, S. B. Org. Lett. 2004, 25, 4775-4778
Analysis
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