Synthesis of N-(3-azido-4-chlorophenyl)-N′-[3H-methyl] thiourea, an efficient photoaffinity probe for the urea carrier

✍ Scribed by Herve Lamotte; Francoise Degeilh; Philippe Neau; Pierre Ripochet; Bernard Rousseau

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: French
• Weight: 362 KB
• Volume: 34
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580340312

✦ Synopsis

Abstract

Starting from commercial 4‐chloro‐3‐nitroaniline, through a 5 step synthesis, was prepared 3‐azido‐4‐chlorophenylisothiocyanate 5 which was reacted with [^3^H]‐methylamine. The latter was obtained by three methods:

[^3^H]‐LiAlT~4~ reduction of benzylcarbamate gave rise to [^3^H]‐methylamine (S.A.: >70 Ci/mmol).

Catalytic reduction of HCN with ^3^H~2~ lead to [^3^H]‐CH~3~NH~2~ (S.A.: 0.7 Ci/mmol).

Schmidt rearrangement of [^3^H]‐sodium acetate gave [^3^H]‐CH~3~NH~2~ (S.A.: 29 Ci/mmol).

Compound 7 at the highest specific activity had a self radiolysis rate precluding its practical use in biological studies whilst 29 Ci/mmol [^3^H]‐7 was satisfactory.