Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)-4-carbonitrile

Round 1

Reviewer 1 Report

The work presents a simplistic synthesis taking a mono-bromide of a somewhat esoteric heterocyclic motif to the corresponding cyano derivative in one chemical transformation. The investigation has obviously not been carried out to a greater depth and instead on can assume that only few experiments have been performed. This means that the methodology devised can hardly be described as the optimum way of achieving the synthesis of the target product. Furthermore, and this must be seen as a severe ctiticism, the preparative description in the experimental section offers 43 mg of the desired target molecule and this is a far too small to saying that the method ustilized is a validated and proven procedure. The minimum requirement at this stage should be that the compound is prepared in at least a 1 g scale, in other words at a more than 20 times larger scale to be able to characterize it as trustworthy. The annotated pdf file of the paper points out a few typos and other shortcomings for the authors to be aware of.   

Comments for author File: Comments.pdf

Author Response

Reviewer 1

The authors are grateful to the reviewer for highly professional review.

Point 1.

The investigation has obviously not been carried out to a greater depth and instead on can assume that only few experiments have been performed. This means that the methodology devised can hardly be described as the optimum way of achieving the synthesis of the target product.

Response from authors.

Additional previously performed reactions to optimize the synthesis of compound 2 are added to the text of the paper.

Point 2.

Furthermore, and this must be seen as a severe ctiticism, the preparative description in the experimental section offers 43 mg of the desired target molecule and this is a far too small to saying that the method ustilized is a validated and proven procedure. The minimum requirement at this stage should be that the compound is prepared in at least a 1 g scale, in other words at a more than 20 times larger scale to be able to characterize it as trustworthy.

Response from authors.

We have synthesized cyanide 2 from 0.5 g of starting bromide 1; in this case, the yield of cyanide 2 only slightly decreased (these data are given in the experimental part of the paper). Therefore, the data presented can be considered reliable enough to be published in this journal.

Point 3.

The annotated pdf file of the paper points out a few typos and other shortcomings for the authors to be aware of.

Response from authors.

Typos have been corrected as suggested by the reviewer.

Round 2

Reviewer 1 Report

The authors have taken the referee's comments onboard in a constructive way and addressed the issues pointed out in a satisfactory manner. This has resulted in a conisderably improved short notice article that is acceptable for publication, except for two remaining items:

The first concerns the variation in yield data reported for the target compound - see file attached - and the discrepancy noted has to be addressed.before

The second is the prior existence of compound 2, as the text indicates that the target molecule might in fact have been prepared previously, albeit using other methods. The authors are requested to clarify this and provide the standard CAS number for product 2 in case there is one.  

 

Comments for author File: Comments.pdf

Author Response

The mistake in the yield of compound in the Table 1 was corrected.

Compound 2 is not described in the literature, and CAS number cannot be given.