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Chris The Great
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[*] posted on 5-11-2005 at 13:55
Methanesulfonyl chloride


R-SO2-Cl

I am searching for a synthesis of methanesulfonyl chloride, or other alkylsulfonyl chloride or arylsulfonyl chloride (preferably methane, but other groups will do if methane will be far too difficult).

I have not found anything relating to the synthesis of these compounds.
I am thinking that SO2Cl2 would be a good starting point but can't see how you could replace a Cl with a CH3 group.
Maybe SO2 + CH3Cl ?
Another idea would be to make toluene sulphonic acid, and then chlorinate with thionyl chloride, if need be.

Any hints, tips or complete procedures are greatly appreciated.

Thanks!
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hinz
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[*] posted on 5-11-2005 at 15:19


Here is an abstract for the synth. of methanesulfuryl chloride using CH4 SO2Cl2 and a free radical starter, in this case anhydrous H2SO4. Maybe anyone can get the whole patent.

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&a...

Maybe by chloriation of dimethyl sulfate?.
Or by this method: CH3Br reacts in ethyl ether (solvent) with Mg, this gives CH3MgBr. Then destill the CH3MgBr and mix (1 mol/1mol) it with sulfuryl chloride. This should give Mg(Br)Cl and CH3SO2Cl

[Edited on 5-11-2005 by hinz]
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[*] posted on 6-11-2005 at 03:28
Synthesis of methanesulfonyl chloride (MSC) from methane and sulfuryl chloride


Communication

Chemical Communications, 2004, (4), 472 - 473
DOI: 10.1039/b314160h
Synthesis of methanesulfonyl chloride (MSC) from methane and sulfuryl chloride

http://rapidshare.de/files/7258127/b314160h.pdf.html




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Axt
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[*] posted on 6-11-2005 at 03:41


Preparation of Methanesulfonyl Chloride
C. R. Noller, P. J. Hearst;
J. Am. Chem. Soc.; 1948; 70(11); 3955-3955. [attached]

Three methods commonly have been used for the preparation of methanesulfonyl chloride, a valuable reagent, namely, by the action of phosphorus pentachloride on sodium methanesulfonate, and by the action of chlorine and water on methyisothiourea or on methyl thiocyanate.

Experimental
In a 200-cc., three-necked flask, fitted with a mechanical stirrer, a reflux condenser, a thermometer and a separatory funnel, and set up in a hood, is placed 152 g. (105 cc., 1.5 moles) of 95% methanesulfonic acid (Standard Oil Co. of Indiana). The acid is heated to 95' on a steam-bath, and 146 cc. (238 g., 2.0 moles) of thionyl chloride (Eastman Kodak Co. grade) is added over a period of four hours. The temperature is kept at 95 throughout the addition, and heating is continued for three and one-half hours after the addition has been completed. The product is transferred to a modified Claisen flask and distilled at reduced pressure, using an oil-bath to supply heat. Most of the thionyl chloride distills at room temperature. A free flame should be avoided, since local superheating causes charring and decomposition. The fumes from the decomposition cause the normally clear product to darken. The bath temperature should not exceed 115" at the end of the distillation. The yield of product distilling at 67-73' (20 mm.) is 122 g. (71% of the theoretical amount).

(peroxide or azide? :P )

[Edited on 6-11-2005 by Axt]

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Chris The Great
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[*] posted on 6-11-2005 at 13:45


Thanks guys! You've saved me!
Also, thanks to Bromic Acid who found the reference Axt posted before I went to bed last night, and thanks to Axt for posting it (saved me the trouble :P )

Axt, not sure what you mean with your peroxide or azide comment, I think those use dimethylsulfate for their prep (well at least the peroxide does).
I am planning on using this to prepare an intermediate epoxide and then aziridine. No explosives this time :D
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[*] posted on 6-11-2005 at 13:57


Yeh, in the future just search pubs.acs.org, If your in luck, like the one above its on one page (anyone can access the first page of the articles).

I'm quite sure NaN3 will get you an azide, Na2O2 a peroxide. Same way acetyl peroxide and benzoyl peroxide are formed from acetyl/benzoyl chloride.
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