1,2,3-Dithiazolyl and 1,2,35-Dithiadiazolyl Radicals as Spin-Bearing ...

Compound Name: 5-chloro-1H-[1,2,5]thiadiazolo[3,4-e][1,2,3]benzodithiazolium
chloride
MW: 282.20 g/mol
Synthesis and Structure:
Appearance:
Green powder
Lit. and/or
notebook # and page:
DM02-6 p10
DM02-22 p45
First made on
date: Nov 13, 2007
MacDonald
Made by: Dan J.
Experimental Data: Sulfur monochloride (11.9421 g, 88.440 mmol) was added to a
homogeneous solution of 5-chlorobenzo[c][1,2,5]thiadiazol-4-amine (2.0155 g, 10.998
mmol) in distilled and degassed acetonitrile (60 mL). A thick, orange precipitate was
formed immediately and over the next hour the solution turned to a brown, heterogeneous
mixture. The reaction mixture was refluxed for 20 h yielding a very dark, opaque
mixture which was filtered hot. The precipitate was washed with 2, 10 mL portions of
distilled acetonitrile and dried under dynamic vacuum to afford the title compound as a
dark green powder (4.3536 g, 15.428 mmol), 140% yield based on 5-
chlorobenzo[c][1,2,5]thiadiazol-4-amine. The high yield an inherent result of elemental
sulfur generated from the large excess of sulfur monochloride require for the reaction to
proceed.
FTIR (KBr): 3040(w), 3005(w), 2950(w), 1553(w), 1518(m), 1482 (s), 1424(m),
1388(w), 1349(s), 1286(w), 1261(w), 1213(m), 1176(w), 11569(w), 1106(m), 1020(m),
934(w), 907(w), 877(m), 861(s), 824(m), 758(m), 720(m), 628(w), 584(w), 505(m),
490(w).
MS (EI + ): m/z 245.9 (parent ion), 178.0 (-SCl).
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