March 2009
Synthesis and Bioactivity of Novel Benzisothiazolone Derivatives
as Potential Microbiocides
323
TMS as internal standard and DMSO-d6 as solvent. The elemen-
tal analyses were performed with a Bruker DALTONICS ana-
lyzer. The MS spectra were taken on a HP-5988A spectrometer.
Procedure for preparation of 7. A mixture of benzoiso-
thiazolone (3.02 g, 0.02 mol commercial from National
Medicine Corporation, Shanghai of China), polyoxymethylene
(5.28 g, 0.022 mol) in 10 mL of chloroform was refluxed for
5 h at 60ꢁC under stirring. Compound 7 (3.13 g, 87%) was
obtained by the usual work-up of the reaction mixture. The
physical and spectral data of compound 7 were in accordance
with the data reported by Morley et al. [4].
(3-Oxobenzo[d]isothiazol-2(3H)-yl)methyl 3,5-dimethylben-
zencarboxylate (11c). This compound (2.16 g, 69%) was obtained
as crystals, mp 109–111ꢁC; 1H NMR (DMSO-d6, 400 MHz) d: 1.27
(m, 6H, 2CH3), 6.10 (s, 2H, CH2), 7.07ꢃ7.79 (m, 7H, Ar-H); MS
(ESI) m/z: 313.4 (Mþ); Anal. Calcd. for C17H15NO3S: C, 65.16; H,
4.82; N, 4.47; Found: C, 64.96; H, 4.45; N 4.41.
Acknowledgments. This work was supported by Natural Sci-
ence Foundation of Hainan Province of China (No. 20503) and
Key Laboratory Open Foundation of Chinese Ministry of Educa-
tion. The authors thank Professor Yongcan Zhou of Hainan Uni-
versity for his help.
General procedure for the synthesis of (3-oxobenzo[d]iso-
thiazol-2(3H)-yl)methyl benzencarboxylates 11a-c. To the
stirred and cooled solution of compound 7 (1.81 g, 10 mmol),
triethylamine (1.22 g, 11 mmol) in 20 mL of acetone (dried
before used) with ice-water bath, benzoyl chloride (1.41 g,
10 mmol) was added dropwise. The colorless precipitates were
obtained as soon as by addition of benzoyl chloride. When
benzoyl chloride was added completely, the ice-water bath
was removed and the resulting mixture was continuously
refluxed for 2 h with stirring. After the reaction quenched, the
reaction mixture was concentrated under reduced pressure, and
purified by column chromatography on silica gel (petroleum
ether:ethyl acetate ¼ 3:1) to gave pure crystals of 11a, mp
114–116ꢁC; 1H NMR (DMSO-d6, 400 MHz) d: 6.15 (s, 2H,
CH2), 7.27ꢃ7.87 (m, 9H, Ar-H); GC-MS (ESI) m/z: 285 (Mþ),
256, 164, 136, 105, 77; Anal. Calcd. for C15H11NO3S: C,
63.14; H, 3.89; N, 4.91; Found: C, 62.87; H, 3.46; N 4.88.
(3-Oxobenzo[d]isothiazol-2(3H)-yl)methyl 4-fluorobenzen-
carboxylate (11b). This compound (2.18 g, 72%) was obtained
as crystals, mp 95–96ꢁC; 1H NMR (DMSO-d6, 400 MHz) d:
6.14 (s, 2H, CH2), 7.07ꢃ7.85 (m, 9H, Ar-H); MS (ESI) m/z:
303.3(Mþ); Anal. Calcd. for C15H10FNO3S: C, 59.40; H, 3.32;
N, 4.62; Found: C, 59.10; H, 3.39; N, 4.57.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet