5,5′-(Piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one)

Round 1

Reviewer 1 Report

Dear Editor, 

After carefully reading the Short Note entitled '5,5'-(Piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiole-3-one)', the reviewer thinks it is suitable for publication in Molbank journal after minor revision. Below are the details:

Introduction.

Lines 24-27: in the reviewer's opinion, it could be helpful to report the structure of oltipraz and its keto derivative to catch the reader's attention to the scaffold's importance.

Lines 49-50: the use of ACN as the solvent, even if it does not increase the yield of final product 3, reduces the reaction time; authors could evidence it in the text.

Lines 57-58: correct the numbering of 5,5'-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiole-3-one) and of 4- chloro-5-piperazin-1-yl-3H-1,2-dithiol-3-one.

supporting information: pages S5-S,  change the numbering of compound 5,5'-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiole-3-one) from 2 to 3.

Author Response

Reviewer 1

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

Point 1.

Lines 24-27: in the reviewer's opinion, it could be helpful to report the structure of oltipraz and its keto derivative to catch the reader's attention to the scaffold's importance.

Response from authors.

The Figure with the structures of Oltipraz and 4-methyl-5-(pyrazin-2-yl)-3H-1,2-dithiol-3-one has been added to the paper as suggested by the reviewer.

Point 2.

Lines 49-50: the use of ACN as the solvent, even if it does not increase the yield of final product 3, reduces the reaction time; authors could evidence it in the text.

Response from authors.

Corrected as suggested by the reviewer.

Point 3.

Lines 57-58: correct the numbering of 5,5'-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiole-3-one) and of 4- chloro-5-piperazin-1-yl-3H-1,2-dithiol-3-one.

Response from authors.

Corrected as suggested by the reviewer.

Point 4.

supporting information: pages S5-S,  change the numbering of compound 5,5'-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiole-3-one) from 2 to 3.

Response from authors.

Corrected as suggested by the reviewer.

Reviewer 2 Report

This manuscript contains the preparation of an interesting compound either directly or via a two-step process.

The manuscript is well written, but some questions need to be addressed. Most of them are minor mistakes.

In the Introduction, line 35 says “selected” does it mean “selective”?

In Results and Discussion, line 48, Entry 2 should be Entry 4.

In Materials and Methods, line 70, the part between parenthesis is out of context. The NMR spectrometer is operating at 300 MHz for 1H-NMR and at 75 MHz for 13C-NMR.

In Materials and Methods, line 95. The Yield of 172g should be 172 mg.

In the Supplementary Materials, both compounds are labeled as 2

However, what should be clarified is the experimental part, as this is the most important contribution of this manuscript.

In the preparation of 2, it is said that “the solvent was distilled, the residue extracted with DCM…” How is that extraction performed? Is water added to form the two phases needed for the extraction?

In the same preparation, it follows that “The solvent was removed, the solid was filtered…” If the solvent was removed, what was the solid filtered of? And then the solid was washed with water? This is not quite clear.

In the synthesis of 3, the same questions arise,

“The precipitate was filtered, washed…” The washed part was solid? Or the clean solution after filtering off the solid?

It would be interesting to include the experimental part of the preparation of 3 from 2

This manuscript can be published after solving those questions.

Author Response

Reviewer 2

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

Point 1.

In the Introduction, line 35 says “selected” does it mean “selective”?

Response from authors.

Corrected as suggested by the reviewer.

Point 2.

In Results and Discussion, line 48, Entry 2 should be Entry 4.

Response from authors.

Corrected as suggested by the reviewer.

Point 3.

In Materials and Methods, line 70, the part between parenthesis is out of context. The NMR spectrometer is operating at 300 MHz for 1H-NMR and at 75 MHz for 13C-NMR.

Response from authors.

Corrected as suggested by the reviewer.

Point 4.

In Materials and Methods, line 95. The Yield of 172g should be 172 mg.

Response from authors.

Corrected as suggested by the reviewer.

Point 5.

In the Supplementary Materials, both compounds are labeled as 2

Response from authors.

Corrected as suggested by the reviewer.

Point 6.

In the preparation of 2, it is said that “the solvent was distilled, the residue extracted with DCM…” How is that extraction performed? Is water added to form the two phases needed for the extraction?

In the same preparation, it follows that “The solvent was removed, the solid was filtered…” If the solvent was removed, what was the solid filtered of? And then the solid was washed with water? This is not quite clear.

In the synthesis of 3, the same questions arise,

“The precipitate was filtered, washed…” The washed part was solid? Or the clean solution after filtering off the solid?

Response from authors.

Corrected as suggested by the reviewer.

Point 7.

It would be interesting to include the experimental part of the preparation of 3 from 2

Response from authors.

The preparation of 3 from 2 has been added to the paper.