Mitotane
From The Cure For The Needy
Contents |
Mitotane (Lysodren)
Effective Against
Mitotane is a derivative of the insecticide DDT and causes direct necrosis and atrophy of the adrenal cortex; it also modifies the peripheral metabolism of steroids.
Cost
From Sigma-Aldrich: 24.60 USD (1g)
Reported Routes of Synthesis
Diazotisation of 2-chloroaniline (I) with NaNO2 and HBr in H2O furnishes 2-chlorobenzenediazonium bromide (II), which is then brominated with CuBr and HBr to afford 1-bromo-2-chlorobenzene (III) (1). Treatment of 1-bromo-2-chlorobenzene (III) with Mg in ether, and condensing the obtained Grignard reagent with dichloroacetaldehyde (IV) in ether yielding 2,2-dichloro-1-(2-chlorophenyl)ethanol (V), which finally condenses with chlorobenzene (VI) in the presence of H2SO4 to provide Mitotane (2).
Snyder, H.R.; Wicks, Z. Jr. o-Chlorobromobenzene. Org Synth Coll 1955, 3: 185
Haller, H.L.; Bartlett, P.D.; Drake, N.L.; Newman, M.S.; et al. The chemical composition of technical DDT. J Am Chem Soc 1945, 67(9): 1591
Please reference Vardnayan, R and Hruby, V. Synthesis of Essential Drugs. Elsevier:2006. pg. 411 for a short synthesis.
Cost of Starting Materials and Selected Reagents:
Starting Material 1-Bromo-2-chlorobenzene from Sigma-Aldrich: 20.8 USD (10 g)
- Magnesium from Sigma-Aldrich: 66.2 USD (500g)
Chlorobenzene from Sigma-Aldrich: 42.2 USD (100 mL)
Sulfuric acid from Sigma-Aldrich: 67.2 USD (100 mL)