N-(1-azido-2-(azidomethyl)butan-2-yl)-4-methylbenzenesulfonamide

Round 1

Reviewer 1 Report

Authors in this paper describes the preparation procedure and physical properties of N‐(1‐azido‐2‐(azidomethyl)butan‐2‐yl)‐4‐methylbenzenesulfonamide, with a very simple preparation sequence.

The reaction is direct, and its description is clear enough.

Some points in the manuscript need to be reviewed and corrected before publication

1)     In the introduction the authors give the importance of bi‐triazole systems as drug precursor, but they do not give any synthetic method of literature precedingly used for their synthesis; it is necessary to give some commented references for the synthesis of bi‐triazole.

2)    In the introduction, the authors say that the class of compound synthesized in this work is different from their previous work, giving 7 references of self-citation. (lines 26-29); it is not necessary to go through the entire bibliography of the authors, 1 or 2 citations, among the most significant of their previous papers, are enough.

3)    the chemical shift values given in the text and in the tables 1 and 2 show too many significant figures (eg. lines 48, 50, 52, 53, 58 etc.). For the proton the accuracy is not higher than a hundredth and for the carbon to the tenth. All values need to be reviewed and approximated.

4)     The 1H-NMR of p-Toluenesulfonil is a second-order AA'XX 'system, so the authors should provide more details of how they derived the J-ortho J-meta coupling constants inserted in the text (lines 51, 57, 109 , 110 and 127) and in Tables 1 and 2.

5)    coupling constants should be given with only a tenth of accuracy (text and tables).

6)    In table 1 and table 2, for the quartet of protons 2, the authors must indicate the resonance and not the interval of the quartet.

7)    In table 1 and table 2, is not clear the meaning of column “Correlation H-H”

8)     In “Materials and Methods” section, is not clear the chemical shift reference used; line 85 “NMR data are listed in ppm and are reported relative to tetramethylsilane” line 86 “residual solvent peaks being used as an internal standard.” Furthermore, the peak of tetramethylsilane is not present in the spectra shown in “Supplementary Files_Compound”

9)    For IR the values for =CH(stretching) and  2960 (N‐H(stretching) are inverted (lines 114 and 130)

Author Response

Dear reviewer

All the Authors thank you for your efforts and comments aimed to improve the quality of our manuscript.

Please find attached the revised version of our manuscript “N-(1-azido-2-(azidomethyl)butan-2-yl)-4-methylbenzenesulfonamide”. You will find below the answers to your comments and suggestions, point by point.

Best regards

Prof. Anouar Alami

1)     In the introduction the authors give the importance of bi‐triazole systems as drug precursor, but they do not give any synthetic method of literature precedingly used for their synthesis; it is necessary to give some commented references for the synthesis of bi‐triazole.

We have added in the text a recent reference concerning the synthesis of bi-triazole systems.

 2)    In the introduction, the authors say that the class of compound synthesized in this work is different from their previous work, giving 7 references of self-citation. (Lines 26-29); it is not necessary to go through the entire bibliography of the authors, 1 or 2 citations, among the most significant of their previous papers, are enough.

 In our subsequent work, we prepared mono and tri-triazole systems. This time, we are talking about the preparation of bi-triazole systems which are different in terms of structure but they will be obtained according to the same principle as the previous ones. This is why we have cited our previous works (7 references).

3)    the chemical shift values given in the text and in the tables 1 and 2 show too many significant figures (eg. lines 48, 50, 52, 53, 58 etc.). For the proton the accuracy is not higher than a hundredth and for the carbon to the tenth. All values need to be reviewed and approximated.

 All values have been reviewed and approximated.

4)     The 1H-NMR of p-Toluenesulfonil is a second-order AA'XX 'system, so the authors should provide more details of how they derived the J-ortho J-meta coupling constants inserted in the text (lines 51, 57, 109, 110 and 127) and in Tables 1 and 2.

5)    Coupling constants should be given with only a tenth of accuracy (text and tables).

 Coupling constants are given with an accuracy of only one tenth (Text and Tables).

6)    In table 1 and table 2, for the quartet of protons 2, the authors must indicate the resonance and not the interval of the quartet.

 The resonance of quartet of protons 2, is indicated in Tables 1 and 2, and also in the text.

7)    In table 1 and table 2, is not clear the meaning of column “Correlation H-H”

 The "Correlation H-H" column shows the data of the two-dimensional spectrum that results from the COSY experiment. The COSY spectra of compounds (2) and (3) have not been added in the Supplementary Materials. If it is necessary, we can add these spectra.

8)     In “Materials and Methods” section, is not clear the chemical shift reference used; line 85 “NMR data are listed in ppm and are reported relative to tetramethylsilane” line 86 “residual solvent peaks being used as an internal standard.” Furthermore, the peak of tetramethylsilane is not present in the spectra shown in “Supplementary Files_Compound”.

 The sentence “residual solvent peaks being used as an internal standard” have been removed from the Text.

9)    For IR the values for =CH(stretching) and  2960 (N‐H(stretching) are inverted (lines 114 and 130)

We have inverted the values for "=CH(stretching)" and "N‐H(stretching)" in the Text.

Author Response File: Author Response.pdf