OneGroup CX Disconnections
:>:e~Group C-X Disconnections
Jimp Ie Examples
(1) H 0 ' 3 H 0 The garden fungicide 'Captan' (2) is made from (1). This is an imide - a double amide - and so both bonds between carbonyl and nitrogen can be disconnected.
knalysis
0f^H imi_de
H COX
The best reagent for the double acyl derivative (3) is the anhydride (4) whose synthesis is discussed in Chapter T 17. Reaction of (4) with ammonia gives TM (1).
Synthesis23
Esters
In making esters, either the alcohol or acid may be in short supply. Precious acids are often treated with a large exccss of the alcohol (e.g. as solvent) with mineral acid catalysis.
MeOII
The potential analgesic (5) is an ester of the alcohol (6), which has to be made (see p T 77), and acid EtCO^H. The chosen reagent was the anhydride which wastes half of the cheap acid but ensures efficient conversion of (6) into (5).
Analysis
Synthesis3Q(a}
Simple Problems
1, Mark all the C-X bonds you would wish to disconnect in these molecules and say why.
H Intermediate in iso-
Cl jNHBU
Cl jNHBU
■NHC02Me
■NHC02Me
Average user rating: 5 stars out of 1 votes
Post a comment