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Synthesis of [14C]-labelled 3-[N-(4-bromophenyl)carbamoyl]-7-chloro-4-hydroxycoumarin and 3-[N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]carbamoyl]-7-chloro-4-hydroxycoumarin

✍ Scribed by Byung H. Lee; Michael F. Clothier

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
196 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The novel [^14^C]‐labelled 3‐carbamoyl‐4‐hydroxycoumarins were prepared in two steps from 4‐chloro‐acetylsalicyloyl chloride (3). The isotope was incorporated by the reaction of diethyl malonate‐1,3‐^14^C with 4‐chloro‐acetylsalicyloyl chloride (3). Subsequent condensation of the resulting 3‐ethoxycarbonyl‐4‐hydroxy‐7‐chlorooumarin (5a) with 4‐bromo‐aniline gave 3‐[N‐(4‐bromophenyl)carbamoyl‐7]‐chloro‐4‐hydroxycoumarin (1a) with a specific activity of 0.7 mCi/mmol. Condensation of (5a) with 2‐amino‐5‐trifluoromethyl‐1,3,4‐thiadiazole gave 3‐[N‐[5‐(trifluoromethyl)‐1,3,4‐thiadiazol‐2‐yl]carbamoyl]‐7‐chloro‐4‐ hydroxycoumarin (2a) with a specific activity of 0.6mCi/mmol.

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