2,1,3-Benzothiadiazole-5-methanol

Benzo [1, 2, 5] thiadiazole-5-carboxylic acid (2. 00g, 11. 1 lmmol) was dissolved in tetrahydrofuran (50mL) and cooled to 0°C. To this was added triethylamine (1. 80mL, 12. 87mmol) followed by isobutylchloroformate (1.62mL, 12. 40mmol) in a dropwise manner. The resulting slurry was stirred for a further 30 minutes at 0°C and then filtered into a mixture of sodium borohydride (0.83g, 21. 84mol) in ice water (20mL). The resulting mixture was stirred at 0°C for 30 minutes, evaporated to one quarter of its volume and then extracted with dichloromethane (3x50mL). The organic phases were combined and then dried over sodium sulfate. This was followed by concentration under reduced pressure to provide the desired product as a white solid which was used without further purification (1. SOg, 81percent).Benzo[1, 2, 5]thiadiazol-5-ylmethanol 6 (115 mg, 0.69 mmol) and MnO2 (241 mg, 2.8 mmol) in CHCl3 (10 mL) were stirred at room temperature overnight. The reaction mixture was filtered on a plug of Celite and the filtrate evaporated to provide 111 mg of pure 2, 1, 3-benzothiadiazole-5-carboxaldehyde 7 (98 %): 1H NMR (300 MHz, CDCl3) delta 10.19(s, 1H), 8.49 (s, 1H), 8.09 (s, 2H).EXAMPLE 214C 2, 1, 3-benzothiadiazole-5-carboxaldehyde 5-Hydroxymethylbenzo-2, 1, 3-thiadiazole (2.6 g, 16 mmol) and manganese dioxide (6.0 g, 64 mmol) in chloroform (150 mL) were stirred at room temperature overnight. The reaction mixture was filtered off and the filtrate was evaporated to provide 1.9 g of the title compound. 1H NMR (CDC13) 8.12 (s, 2H), 8.51 (m, 1H), 10. 21 (s, 1H).The 5-Hydroxy-methylbenzo-2, 1, 3-thiadiazole (2, 6 g, 16 mmol) and MnO2 (5.6 g, 64.41 mmol) in CHCl3 (150 mL) were stirred at room temperature (approximately 25 C.) overnight. The reaction mixture was filtered and the filtrate evaporated. Crude residue was submitted to the chromatograph on silica gel (EtOAc/Hexane, 7/3, v/v) to provide 1.9 g of 2, 1, 3-benzothiadiazole-5-carboxaldehyde. m.p. 93 C. ESI-MS (Mw 164.18): 165.2 (M+H+). 1H-NMR (DMSO-d6): 10.21 (s, 1H), 8.78 (d, 1H), 8.19 (d, 1H), 8.04 (s, 1H).EXAMPLE 214B EXAMPLE 3 Isophthalic acid di-(2, 1, 3-benzothiadiazol-5-yl)methyl ester By following the general method of Example 1, 1, 3-benzenedicarbonyl chloride was reacted with Example 22 Preparation of

Molecular Weight:166.20
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:166.02008399
Monoisotopic Mass:166.02008399
Topological Polar Surface Area:74.2
Heavy Atom Count:11
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes