2(3H)-Benzothiazolone,7-chloro-(9CI)

(b) 7-Chloro-2(3H)-benzothiazolone Prepared analogous to Example 2(b) from 3-acetyl-7-chloro-2(3H)-benzothiazolone with a yield of 90% of theory. M.p. 202-203 C. (1, 2-dichloro-ethane). C7 H4 ClNOS (185.63)-- Calc.: C-45.29%; H-2.17%; Cl-19.10%; N-7.55%; S-17.27%. Found: C-45.24%; H-2.26%; Cl-19.40%; N-7.64%; S-17.20%.(c) 7-Chloro-2(3H)-benzothiazolone Prepared analogous to Example 5 from 7-chloro-2-ethoxy-benzothiazole and concentrated hydrochloric acid with a yield of 38% of theory. M.p.: 202-203 C. (after recrystallization from methanol and from diisopropyl ether). C7 H4 ClNOS (185.63)-- Calc.: C-45.29%; H-2.17%; Cl-19.10%; S-17.27%. Found: C-45.15%; H-2.19%; Cl-19.23%; S-17.43%.STR130 A mixture of 29.0 g (0.09 mole) of 7-chloro-2-benzylaminocarbonyl-benzothiazole 3-oxide and 150 ml of toluene is heated at 90 C., 13.8 g (0.09 mole) of phosphoryl chloride (phosphorus oxychoride, POCl3) are added dropwise to the mixture, and the reaction mixture is stirred at 90 C. for 3 hours. When the reaction mixture has cooled down, the 7-chloro-2-benzothiazolone crystals, which have been formed as the product of a side reaction, are filtered off with suction and the solvent is distilled off the filtrate under a water pump vacuum. The residue is chromatographed over a silica gel column, using chloroform as the solvent. 19.0 g (66% of theory) of 7-chloro-3-benzylaminocarbonyl-2-benzothiazolone of melting point 106 C. are obtained. The compounds of the formula (I) listed in Table 3 below can be prepared in analogy to Example 1.

Molecular Weight:185.63
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:184.9702126
Monoisotopic Mass:184.9702126
Topological Polar Surface Area:54.4
Heavy Atom Count:11
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes