Dear Osama,

Using of PhP3/N-halosuccinimide in CH2Cl2 at RT afforded alkyl halide from thiol. See: https://www.google.com.eg/url?sa=t&rct=j&q=&esrc=s&source=web&cd=10&cad=rja&uact=8&ved=0ahUKEwiMsc3ynOLOAhVRkRQKHfp2D3oQFghZMAk&url=https%3A%2F%2Fwww.thieme-connect.com%2Fproducts%2Fejournals%2Fabstract%2F10.1055%2Fs-2001-15157&usg=AFQjCNFLVPyaJPAz9VszzvpI5aJ9uy1JqA&sig2=fEec-Y3Qtm_S1A_ayHQveA

Dear Osama,

You may need to convert the SH firstly to OH fusion with NaOH and or/KOH and then reacting the product you get with POCl3 or PCl5 to get Cl in place of SH

Dear Osama,

The fusion of thiol with NaOH-KOH may be not effective method to convert it to OH. You may obtained disulphide and desulfrused product combined with low yied of phenolic OH. Please, read the attachment paper.

Find in attach a report article on: Fused Salt Reactions of Organosulfur Compounds

Michael A. Nowak, Bruce R. Utz, Daniel J. Fauth and Sidney Friedman

U.S. Department of Energy

Pittsburgh Energy Technology Center

Dear Osama,

I suggest you to oxidize SH to SO3H ( sulphonic acid group) and then convert the later to OH by reacting it with NaOH, then reacting the OH compound with PCl3 and or PCl5 to get Cl atom in place.

Oxidation of thiols to sulphonic acids with Oxone®/NaHCO3 and KBrO3

Oxone is Potassium peroxymonosulfate is widely used as an oxidizing agent. It is the potassium salt of peroxymonosulfuric acid. Wikipedia

Formula: KHSO5

Molar mass: 152.2 g/mol

Link: Authors: https://www.google.com.eg/url?sa=t&rct=j&q=&esrc=s&source=web&cd=4&cad=rja&uact=8&ved=0ahUKEwiShL2Kq-LOAhVMWhQKHckVDSUQFgg8MAM&url=http%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2Fslct.201600028%2Ffull&usg=AFQjCNE7DR6c8t8kDEgSo42k6iEwJI1lKA&sig2=qzkax3juHyhqoB_7cqxC1Q

Best wishes

Sulfonic acids are formed by the vigorous oxidation of thiols or disulfides with KMnO4 or nitric acid (HNO3). See ( eq. 10-54) in the attached file

Oxidation of thiols and disulfides to sulfonic acids

US 3948922 A

Abstract

A process for formation of a sulfonic acid through oxidation of a thiol or disulfide. The process is carried out in the presence of a sulfoxide such as dimethyl sulfoxide, a halogen or hydrogen halide catalyst, and an excess quantity of water. The water acts as a moderator for the oxidation reaction to reduce the level of decomposition of the sulfoxide and, thereby, to improve the overall efficiency of the process.

See link: https://www.google.com.eg/url?sa=t&rct=j&q=&esrc=s&source=web&cd=21&cad=rja&uact=8&ved=0ahUKEwiShL2Kq-LOAhVMWhQKHckVDSUQFgh-MBQ&url=http%3A%2F%2Fwww.saplinglearning.com%2Fmedia%2Floudon%2Floudon5ech10sec09.pdf&usg=AFQjCNHLmZ8Ioda7mAFkBfh1YC6_sFsQpA&sig2=Qy60wsQuSnoCRomBupShqw

In attach,  a paper on:  THE CHEMISTRY OF THIOL OXIDATION AND DETECTION

Mauro Lo Conte and Kate S. Carroll*

Department of Chemistry, The Scripps Research Institute, Jupiter, FL 33458, United States

In attachment,: MeReO3-Catalyzed Selective Oxidation of Thiols to Sulfonic Acids

Thanks Prof. Dr. Talaat for your kind help and these valuable information.

Sincerely,

Your student Osama Nasr

Dear Osama,

I wish you good luck

Is this an aromatic nitrogen heterocycle?  We published a paper describing the preparation of 2-chlorobenzimidazoles from benzimidazole-2-thiones by first oxidizing the thione to the sulfonic acid with sodium percarbonate in H2O then reacting the sulfonic acid with PCl5 in POCl3 under reflux.  At the time we needed several hundred grams of 2,5,6-trichlorobenzimidazole which previously could only be prepared  with great difficulty in very low yield. The major problem with potassium permanganate is that removal of MnO2 is tedious and difficult.  See Syn. Comm (1998) 28(9), 1703-1712.  Hope this is useful. 

Dear Jack. The method mentioned in your paper is quite good, I hope it works well with Osama.

I  can  send  papers  in  this  field  to  answer  your  question,  by  my  e-mail  ((  [email protected]))  or   ((  [email protected]  ))  

Dear Nagham

By reading your article, i found it nice, however, i didn't find the transformation of SH to Cl.

Best wishes

To substitute -SH by Chlorine atom reflux your compound in excess of POCl3 - 4 to 5-hrs. & remove excess of POCl3 by distillation under vacuum.on cooling  chloro compound separate out.

Dear Madhukar,

Using POCl3 is very useful known method for converting -OH to Cl, however, to use it to convert -SH to Cl, it didn't see before. Do, you've ant reference about it?

Best regards

Dear Madhukar,

I always respect your suggestions.

Using POCl3 is very useful known method for converting -OH to Cl, however, to use it to convert -SH to Cl, it didn't see before. Do, you've any reference about it?

Best regards