PAPER
Sulfonyl Chlorides from S-Alkylisothiourea Salts
1681
Colorless crystals; on a 5-mmol scale, yield: 1.274 g (99%); on a 50-
mmol scale, yield: 12.05 g (99%); mp 89–90 °C (Lit.13 86 °C).
1H NMR (400 MHz, CDCl3): δ = 3.85–3.75 (m, 4 H), 2.32–2.27 (m,
(p) Eckroth, D. R.; Love, G. M. J. Org. Chem. 1969, 34,
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Liskamp, R. M. J. Bioorg. Med. Chem. 2011, 19, 2397.
(t) Merkx, R.; Brouwer, A. J.; Rijkers, D. T. S.; Liskamp, R.
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4 H).
2-Phthalimidoethanesulfonyl Chloride (3q)
Colorless crystals; yield: 0.848 g (62%); mp164–166 °C (Lit.26
160–161 °C).
1H NMR (400 MHz, CDCl3): δ = 7.91–7.76 (m, 4 H), 4.38–4.31 (m,
2 H), 4.18–4.07 (m, 2 H).
(w) Borthakur, S. K.; Boruah, P.; Goswami, B. N. J. Chem.
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Chem. Soc. 1953, 75, 5053. (y) Jensen, F. R.; Brown, H. C.
J. Am. Chem. Soc. 1958, 80, 4038. (z) Jensen, F. R.; Brown,
H. C. J. Am. Chem. Soc. 1958, 80, 4042. (aa) Jensen, F. R.;
Brown, H. C. J. Am. Chem. Soc. 1958, 80, 4046.
2-Methoxyethanesulfonyl Chloride (3r)27
Yellowish oil; yield: 0.714 g (90%).
1H NMR (400 MHz, CDCl3): δ = 3.97–3.94 (m, 4 H), 3.43 (s, 3 H).
Methanesulfonyl Chloride (3s)10
Colorless oil; yield: 7.09 g (62%).
1H NMR (400 MHz, CDCl3): δ = 3.68 (s, 3 H).
(3) For selected examples, see: (a) McKew, J. C.; Lee, K. L.;
Shen, M. W. H.; Thakker, P.; Foley, M. A.; Behnke, M. L.;
Hu, B.; Sum, F.-W.; Tam, S.; Hu, Y.; Chen, L.; Kirincich, S.
J.; Michalak, R.; Thomason, J.; Ipek, M.; Wu, K.; Wooder,
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Clark, J. D. J. Med. Chem. 2008, 51, 3388. (b) Blake, J. F.;
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Autry, C. L.; Bhattacharya, S. K.; Freeman-Cook, K. D.;
Hayward, M. M.; Hulford, C. A.; Nelson, K. L.; Xiao, J.;
Zhao, X. WO 2008129380, 2008. (d) Li, H.; Argade, A.;
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Helv. Chim. Acta 1959, 42, 1653. (b) Albright, J. D.; Benz,
E.; Lanzilotti, A. E.; Goldman, L. Chem. Commun. 1965,
413. (c) Fujita, S. Synthesis 1982, 423. (d) Barco, A.;
Benetti, S.; Pollini, P.; Tadia, R. Synthesis 1974, 877.
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Acknowledgment
The project was supported by The National Basic Research Pro-
gram of China (No. 2013CB328900) and National Natural Science
Foundation of China (Nos. 21172017 and 20092013).
Supporting Information for this article is available online at
nnfomartit
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Synthesis 2013, 45, 1675–1682