反应详情

The title compound was prepared by a modification of a procedure reported for related compounds: Henichart, J. P.; Bernier, J. L. Synthesis 1980, 4, 311. Acetic hydrazide (3.7 g, 50 mmol) in ethanol (50 mL) was placed in a 200 mL 3-necked round bottomed flask outfitted with a magnetic stir bar and a reflux condenser. 2-morpholinoethyl isothiocyanate (8.61 g, 500 mmol) in ethanol (50 mL) was added to the pot. The mixture was refluxed, under N2, for 6 h. The reaction was cooled to room temperature and the solvent removed on the rotovap. The resulting resin was dissolved in minimal ethanol and ether. A white solid precipitated out, was filtered and washed with cold ether. The filtrate, containing uncyclized intermediate, was concentrated and dissolved in xylenes. The mixture was refluxed under N2 for 8 h, then allowed to sit at room temperature, under N2. for 48 h. A white solid formed, was filtered and washed with cold ether. The first and second batches of white solid were combined to yield 7.33 g (64%) of the desired product. 1H NMR (DMSO-d6): d 2.33 (s, 3H) 2.41 (m, 4H) 2.55 (m, 2H) 3.52 (m, 4H) 3.99 (t, 2H, J=6) 13.41 (s, 1H). MS (APCI) calcd for C9H16N4OS: 228.32; found (M+H+) 229.1.

1. customThe title compound was prepared by a modification of a procedure
2. customSynthesis 1980, 4, 311
3. customoutfitted with a magnetic stir bar and a reflux condenser
4. temperatureThe mixture was refluxed, under N2, for 6 h
5. customthe solvent removed on the rotovap
6. dissolutionThe resulting resin was dissolved in minimal ethanol
7. customA white solid precipitated out
8. filtrationwas filtered
9. washwashed with cold ether
10. additionThe filtrate, containing uncyclized intermediate
11. concentrationwas concentrated
12. dissolutiondissolved in xylenes
13. temperatureThe mixture was refluxed under N2 for 8 h
14. customto sit at room temperature, under N2
15. customA white solid formed
16. filtrationwas filtered
17. washwashed with cold ether