A modified synthesis of tritium labelled amides from labelled carboxylic acids and amines using EEDQ as a reagent

✍ Scribed by W. Soudijn; I. van Wijngaarden; A. G. Knaeps

• Publisher: John Wiley and Sons
• Year: 1978
• Tongue: French
• Weight: 243 KB
• Volume: 14
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580140303

✦ Synopsis

T h e r e a c t i o n conditions for t h e p r e p a r a t i o n of a m i d e s f r o m l a b e l l e d c a r b o x y l i c a c i d s and a m i n e s u s i n g EEDQ (2-ethoxy-l(2H)-quinolinecarboxyl i c a c i d , e t h y l e s t e r ) a s a r e a g e n t w e r e m o d i f i e d f o r the s y n t h e s i s of t h e t r i t i u m l a b e l l e d b e n z a m i d e H a l o p e m i d e ( N -2-0x0-1 H -b e n z i m i d a z o l -1 -yl)-1 -p i p e r i d i n y l e t h y l -4 -f l u o r o b e n z a m i d e ) , a s E E D Q , r e a c t e d i n a n unexpected w a y , r e s u l t i n g i n a 1 : l m i x t u r e of t h e b e n z a m i d e and t h e N -c a r b e t h o x y d e r i v a t i v e of t h e s t a r t i n g a m i n e and of " u n r e a c t e d " c a r b o x y l i c a c i d . T h e b a s i c i t y of t h e s t a r t i n g a m i n e i n f l u e n c e d t h e yield of t h e b e n z a m i d e . By o p t i m a l i z i n g the r e a c t i o n conditions, i t w a s p o s s i b l e t o c o n v e r t t h e l a b e l l e d b e n z o i c a c i d quantitatively into t h e b e n z a m i d e . 2 -4 -( 5 -c h l o r o -2 , 3-dihydro-1 y 227