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Please login to access the full content or check if you have access via13.9.2.1.1.1 Method 1: From 2-Aminobenzenethiols
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Wilkins, D. J.; Bradley, P. A., Science of Synthesis, (2004) 13, 268.
The simplest and most common process for the synthesis of 1,2,3-benzothiadiazoles is through the diazotization of 2-aminobenzenethiols. Jacobson prepared the parent compound, 1,2,3-benzothiadiazole in this way,[18] and later extended the reaction to naphtho derivatives.[57,58] The 1,2,3-benzothiadiazole is typically formed by diazotization of the 2-aminobenzenethiol with nitrous acid (Scheme 20). Jacobson also reported that 1,2,3-benzothiadiazole is formed on boiling diazotized bis(2-aminophenyl) disulfide in water.[18] Diazotization of 2-[(phenylsulfanyl)methyl]aniline in water results in the formation of 1,2,3-benzothiadiazole through an initial debenzylation of the sulfide.[59,60] Cadogan and co-workers reported the preparation of 1,2,3-benzothiadiazole (36, R1 = H) in 70% yield by the thermal decomposition of the diazonium acetates, which avoids the variable yields sometimes experienced in the diazotization of 2-aminobenzenethiols.[61] Other methods of preparing 2-aminobenzenethiols have been well documented, and include displacement reactions of 2-chloroanilines with sodium sulfide, and reduction of 2-nitrobenzenethiol (see Houben–Weyl, Vol. E 8d, p 59). A variety of heterocyclic rings have been fused onto the 1,2,3-thiadiazole ring using this method. For example, 1,2,3-thiadiazolopyrimidines have been synthesized by reaction of aminopyrimidinethiols with sodium nitrite and hydrochloric acid.[62]
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References
[18] | Meeeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 888. |
[57] | Meeeeeee, M.; Mee, M., Mee. Meeee. Meee. Mee., (8888) 88, 888. |
[58] | Meeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
[59] | Meeeeee, M.; Meeeeee, M. M., M. Meee. Mee., (8888), 88. |
[60] | Meeeeeee, M.; Meeeeee, M., Meee. Mee. Meee. Me., (8888) 88, 888. |
[61] | Meeeeee, M.; Meeeeee, M. M. M.; Meeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
[62] | Meee, M. M., M. Meee. Mee., (8888), 8888. |
[63] | Müeee, M.; Meeeeeeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8e, 88.