𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The synthesis of [U-14C phenyl] LS 840606, an agricultural fungicide

✍ Scribed by G. Madegard; P. Mestre; P. Raimond; J-P. Noël

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
355 KB
Volume
36
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

2,2′4′‐Trichloro‐[ring U‐^14^C]acetophenone 3 was the key intermediate of this synthesis patterned after the industrial route. An unexpected poor yield was observed during the preparation of 3 by the Friedel‐Crafts reaction of chloroacetyl chloride with 1,3‐dichloro‐[U‐^14^C]benzene 10, possibly the result of an isotope effect although this poor yield might be explained by other factors.

Two routes were checked for the preparation of 1,3‐dichloro‐[U‐^14^C]benzene 10. The action of CCL~4~ with 1,3‐dinitro‐[U‐^14^C]benzene at 280°C was entailed with explosions. A safer route started from [U‐^14^C]aniline via 2,4‐dichloro‐[ring U‐^14^C]acetanilide.

Friedel‐Crafts reaction of 10 with acetyl chloride gave rise in 52% yield to 2′,4′‐dichloro‐[ring U‐^14^C]acetophenone 16 which was brominated to 2‐bromo‐2′,4′‐dichloro‐[ring U‐^14^C]acetophenone 17;17 was condensed with 2,2‐(ethylenedioxy)ethylmagnesium bromide to compound 18; 18 was condensed with 1,2,4‐triazole to 5 then successively treated with HCl:water:dioxane and 2,2,2‐trifluoroethanol/HCl. Separation of the two diastereomers by medium pressure liquid chromatography. 7% overall radioactive yield from [U‐^14^C]aniline. Radiochemical purity 99%.

📜 SIMILAR VOLUMES

An improved synthesis of [phenyl-14C(U)]
An improved synthesis of [phenyl-14C(U)] Lawsone
✍ Christopher Wright; Giliyar V. Ullas 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 French ⚖ 71 KB

## Abstract Synthesis of ^14^C‐labelled Lawsone or 2‐hydroxy‐1,4‐naphthoquinone was achieved by auto‐oxidation of [phenyl‐^14^C(U)]α‐tetralone; the latter was prepared from [^14^C(U)] benzene in a reaction sequence more convenient than reported earlier. Copyright © 2002 John Wiley & Sons, Ltd.

Practical synthesis of 14C S-ribosyl-l-h
Practical synthesis of 14C S-ribosyl-l-homocysteine uniformely labelled on the sugar moiety. An enzymatic route from (U-14C) adenosine
✍ G. Guillerm; B. Allart 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 French ⚖ 227 KB

## Abstract [(U‐^14^C) S‐Ribosyl]‐L‐homocysteine has been prepared enzymatically from (U‐^14^C) adenosine in two steps using S‐adenosyl homocysteine hydrolase (EC.3.31.1) and bacterial S‐adenosyl homocysteine nucleosidase (EC.3.2.2.9) as catalysts.