2
$\begingroup$

The IUPAC name of chlordiazepoxide is given as : 7-chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide, but when I started numbering the structure, I am unable to find chlorine on 7th carbon, it is on 10th. Then why 7-chloro... is given is it wrong? Or I am wrong? Please help by numbering the structure in a diagram even on a paper an upload the photo.

$\endgroup$
6
$\begingroup$

The parent structure of chlordiazepoxide consist of the heteromonocyclic component 2⁠H-1,4-diazepine that is fused to a benzene ring.

2H-1,4-diazepine

According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), the name of the fused parent structure is generated as follows:

P-25.2.2.4 Heteromonocyclic components fused to a benzene ring

Unless listed as a retained name (…), a benzene ring fused to a heteromonocycle of five or more members (a benzoheterocycle) is named by placing the locant(s) indicating the position(s) of the heteroatom(s) at the front of the name consisting of the fusion prefix ‘benzo’ followed by a retained name, a Hantzsch-Widman systematic name, or a name formed by skeletal replacement (‘a’) nomenclature (…). The locants cited correspond to the full bicyclic structure. As in Hantzsch-Widman names, locants are placed in the order corresponding to the order of citation of the heteroatoms in the heterocyclic component. The locant ‘1’ is always assigned to the atom of the heterocyclic component next to a fusion atom. Heteroatoms are allocated lowest locants as a set, without regard to kind; if there is a choice, lowest locants are assigned in accordance with the seniority of the ‘a’ prefixes (…). In general nomenclature locants may be omitted when the name is unambiguous; for preferred IUPAC names locants must be cited. The letter ‘o’ of the ‘benzo’ prefix is elided when followed by a vowel. Indicated hydrogen is placed at the front of the name, when required.
(…)

Accordingly, the name ‘benzodiazepine’ consists of the prefix ‘benzo’ followed by the name ‘diazepine’. The locant ‘1’ is assigned to the atom of the heterocyclic component next to a fusion atom and the heteroatoms are allocated lowest locants as a set (here: 1,4):

3H-1,4-benzodiazepine

The same numbering of locants applies to the complete structure of 7-chloro-2-(methylamino)-5-phenyl-3⁠H-1,4-benzodiazepine 4-oxide:

7-chloro-2-(methylamino)-5-phenyl-3H-1,4-benzodiazepine 4-oxide

$\endgroup$
2
  • $\begingroup$ So is it correct that we should not number the fused carbons? $\endgroup$
    – JM97
    Feb 22 '16 at 15:32
  • $\begingroup$ @JM97 That is correct. If you need to number the fusion carbon atoms, they are given the same number as the immediately preceding nonfusion skeletal atom, modified by a letter ‘a’, ‘b’, ‘c’, ‘d’, etc. $\endgroup$
    – user7951
    Feb 22 '16 at 15:36

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.