Pesin, V. G. published the artcileChemistry of 2,1,3-thiadiazole. V. Nitration of some mono- and dihalo derivatives of benzo-2,1,3-thiadiazole, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Zhurnal Obshchei Khimii (1957), 2599-604, database is CAplus.
cf. C.A. 52, 3790i. Nitration of 2.5 g. 6-chlorobenzo-2,1,3-thiadiazole in 10 ml. concentrated H2SO4 at 0° with 1 ml. concentrated HNO3 and 3 ml. H2SO4, finally 45 min. at 20° gave 2.9 g. 4-nitro-5-chlorobenzo-2,1,3-thiadiazole, m. 141°, which with Fe-aqueous AcOH gave a 4-amino analog (I), m. 92°. Similarly were prepared: 92% 4-nitro-5-bromobenzo-2,1,3-thiadiazole, m. 122°, and its 4-amino analog, m. 114°; also, 4-nitro-5,7-di-chlorobenzo-2,1,3-thiadiazole, m. 127-8°, and its 4-amino analog, m. 171°. Treatment of 0.93 g. I in 6 ml. 98% AcOH with 0.65 g. dichloramine with 1.5 ml. concentrated HCl and 6 ml. AcOH at 12° gave yellow 4-amino-5,7-dichlorobenzo-2,1,3-thiadiazole, m. 171°. Nitration of 4,6-dibromobenzo-2,1,3-thiadiazole as above gave 97% 7-nitro derivative, m. 155.5-56°, which reduced to the 7-amino derivative, m. 160°. Treatment of 4-amino-5-bromobenzo-2,1,3-thiadiazole with Br2 in AcOH gave 4-amino-5,7-dibromobenzo-2,1,3-thiadiazole, m. 162-3°. To 370 g. PhNH2 in 370 ml. MePh was added at 50-60° 400 ml. SOCl2 in 400 ml. MePh, the last part being added at 100°; heating 30 hrs. gave 85% thionylaniline, b. 198-200°. To 39 g. SnCl4 in 80 ml. concentrated HCl at 60° was added in 1 hr. 10 g. 4-bromo-2-nitroaniline, yielding after 1 hr. after treatment with NaOH 88.1% 4-bromo-1,2-diamino-benzene, which (7.5 g.) in 12 ml. MePH was treated with 12 ml. thionylaniline and heated 1 hr. on steam bath, then treated with 4% HCl, yielding 96.5% 5-bromobenzo-2,1,3-thiadiazole, m. 61°. Similar treatment of 3,5-dibromo-ο-phenylenediamine gave 98% 4,6-dibromobenzo-2,1,3-thiadiazole, m. 127-8°.
Zhurnal Obshchei Khimii published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.
Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica