2-(2,3-dihydrobenzofuran-5-yl)-1-Morpholinoethanethione synthesis
- Product Name:2-(2,3-dihydrobenzofuran-5-yl)-1-Morpholinoethanethione
- CAS Number:97483-11-9
- Molecular formula:C14H17NO2S
- Molecular Weight:263.36
110-91-8
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Yield:97483-11-9 52%
Reaction Conditions:
with toluene-4-sulfonic acid;sulfur at 130; for 10 h;
Steps:
1.2
2-(2,3-Dihydrobenzofuran-5-yl)-1-morpholin-4-yl-ethanethione: A mixture of 1-(2,3-dihydrobenzofuran-5-yl)ethanone (7.0 g, 43.20 mmol), morpholine (5.2 g, 60.49 mmol), sulfur (1.38 g, 43.20 mmol) and p-toluenesulfonic acid (0.164 g, 0.86 mmol) was heated at about 130° C. for about 10 hours. At ambient temperature, methanol (35 mL) was added. The solution was cooled in ice and the resulting precipitate was collected by filtration and washed with methanol to afford the title product as a brown solid (5.0 g, 52%). m.p. 141-143° C.; 1H NMR (400 MHz, CDCl3) δ 3.19 (t, J=8.7 Hz, 2H), 3.44 (t, J=4.6 Hz, 2H), 3.66 (t, J=4.8 Hz, 2H), 3.74 (t, J=4.9 Hz, 2H), 4.26 (s, 2H), 4.35 (t, J=4.8 Hz, 2H), 4.56 (t, J=8.7 Hz, 2H), 6.72 (d, J=8.3 Hz, 1H), 6.99 (d, J=8.3 Hz, 1H), 7.22 (s, 1H); IR (KBr) υ 2907, 2852, 1492, 1431, 1256, 1109 cm-1; MS 264 (M+1).
References:
US2009/5431,2009,A1 Location in patent:Page/Page column 31
496-16-2
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