Flame Azalea – Rhododendron calendulaceum

by | Dec 19, 2023 | Azalea

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Dimetotiazine (INN) is a phenothiazine drug used for the treatment of migraine. It is a serotonin antagonist and histamine antagonist.[1]

Synthesis

Thieme Patent:[2]

The Sandmeyer reaction on o-(4-Dimethylaminosulfonyl-2-nitrophenylthio)aniline [5510-56-5] (1) gives 4-[(2-Bromophenyl)-thio]-N,N'-dimethyl-3-nitro-benzenesulfonamide [5510-58-7] (2). The reduction of the nitro group gives 3-Amino-4-((2-bromophenyl)thio)-N,N-dimethylbenzenesulfonamide [5592-64-3] (3). Goldberg reaction gives the chief precursor, 2-Dimethylaminosulfonylphenthiazine [1090-78-4] (4). Alkylation of this with 1-chloro-N,N-dimethylpropan-2-amine [53309-35-6] (5) give Dimethothiazine (6).

References

  1. ^ Shimazawa M, Hara H, Watano T, Sukamoto T (August 1995). "Effects of Ca2+ channel blockers on cortical hypoperfusion and expression of c-Fos-like immunoreactivity after cortical spreading depression in rats". British Journal of Pharmacology. 115 (8): 1359–68. doi:10.1111/j.1476-5381.1995.tb16624.x. PMC 1908864. PMID 8564192.
  2. ^ GB 814512  (1959 to Rhone-Poulenc).


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