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doi:10.1016/S0040-4039(00)83957-X 
Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.
Pamela J. Durham and Robert A. GalemmoJr. , *
Rorer Group, Inc., Pharmaceutical Research and Development Division Fort Washington, PA 19031 U.S.A.
Received 30 August 1985.
Abstract
The use of a new sulfamoylation reagent, N-carbo-(trimethylsilyloxy)sulfamoyl chloride (3) has led to an abbreviated and high yielding preparation of 3-amino-4-N-alkyl-5-aryloxy-1,2,4,6-thiatriazine-l, 1-dioxides (1). A related approach to the 2-N-alkyl isomer (2) is described.
References
BASF, W. German Patent 3,1K3,381 (1983); W. German Patent 3,134,145 (1983); W. German Patent 2,933,889 (1979); US Patent 4,426,219 (1984).
ICI, W. German Patent 2,508,832 (1975).
Merck, US Patent 4,497,810 (1985).
Hoechst, European Patent 0,104,611 (1984).
S.J. Cousins, B.C. Ross, G.N. Maw and J.D. Micheal Tet. Lett. 26 8 (1985), p. 1105. Abstract | 
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J.D. Micheal, P.M. Rees and B.C. Ross Tet. Lett. 26 8 (1985), p. 1101.
Y. Nakayoma and Y. Sanemitsu J. Heterocyclic Chem. 21 (1984), p. 1553.
Compounds
are prepared in two steps from the corresponding primary amine: P.H. Benders J. Royal Netherlands Chem. Soc. 95 9 (1976), p. 217.
P.H. Benders and J.T. Hackmann Recueil Chim. Pays Bas. 91 (1972), p. 343.
R. Appel and G. Berger Chem. Ber. 91 (1958), p. 1339. Full Text via CrossRef
R. Graf Chem. Ber. 92 (1959), p. 509. Full Text via CrossRef
90 MHz 1H NMR (CCl4, CH2Cl2 standard) δ: 8.8 (s, 1H), 4.3 (t, J=8Hz, 2H), 1.15 (t, J=8Hz, 2H) and 0.1 (s, 9H).
Reagent 3.:One equivalent of 2-(trimethylsilyl)ethanol was added drop-wise to a 2M solution of chlorosulfonyl isocyanate in 4:1 carbontetrachloride: hexane at ambient temperature. During the addition the reaction temperature rose from 25 to 40° C and the mixture was allowed to stir for 1h. After removal of the solvent,
was isolated in 100% yield as a low melting solid (m.p. <40°) and was used directly in sulfamoylations. 90MHz 1H NMR (CCl4, CH2Cl2 standard) δ : 8.6 (s, 1H) and 0.1 (s, 9H);IR 1740 (s), 1720 (s), 1410 (s), 1350 (s), 1160 (s) and 1050 (s).
Compounds
,
and
gave satisfactory combustion analyses. The 1H NMR, infrared and mass spectra were In agreement with their proposed structures.
E. Grigat and R. Putter Chem. Ber. 31 (1964), p. 3027. Full Text via CrossRef
J.A. Kloek and K.L. Leschinsky J.Org. Chem. 41 25 (1976), p. 4028. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (24)
The approximate times for the complete conversion of
to
were for
: 1h,
: 0.25h, 9
: 3h. Reactions were monitored by TLC.
