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DBU in Reactions with Saccharin Derivatives
1941
with brine (15 mL) and saturated aqueous sodium sulfite (20 mL),
and dried over sodium sulfate. 3-[30-(100-Azepin-200-onyl)propylamino]-
1,2-benzisothiazole-1,1-dioxide 2 was isolated as a colourless solid by
evaporation to dryness followed by flash column chromatography
using ethyl acetate (25 mg, 8%), m.p. 212–213ꢀC (from EtOH), (Found:
C, 57.41; H, 6.35; N, 12.57. C16H21N3O3S requires C, 57.29; H, 6.31; N,
12.53%); ꢀmax(nujol)/cmÀ1 1612, 1304 and 1152; ꢁH(400 MHz; CDCl3)
1.50–1.94 (8H, m), 2.55 (2H, t, J 5.6), 3.4 (2H, t, J 7.4), 3.40–3.60
(4H, m), 7.50–7.70 (2H, m), 7.78–7.82 (2H, m), 8.74 (1H, s);
ꢁC(300 MHz; CDCl3) 23.8, 26.6, 28.5, 30.2, 37.4, 39.0, 45.4, 50.3, 122.0,
122.1, 128.8, 133.1, 133.4, 142.9, 160.0, 178.6; m/z (EI) 335.13036 (Mþ,
8%. C16H21N3O3S requires 335.13036), 140 (100) and 41 (44).
ACKNOWLEDGMENT
This investigation has enjoyed the support of Payame Noor
University, Iran.
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Received in the USA September 16, 2002