Ethanesulfonyl chloride

A mixture of 76 g. (1.0 mole) of thiourea and 85 g. (0.55 mole) of diethyl sulfate (Caution—toodc substance) is heated in an oil bath. At a temperature of about 130-140° a vigorous exothermic reaction 

A solution of 200 g. (1.0 mole) of the above salt in 800 ml. of water is cooled to 0°, and 500 g. of crushed ice is added. Chlorine gas is introduced into the solution with stirring until decomposition of the isothiuronium salt is complete (see below). The mixture is held at a temperature below 10° during this operation. The sulfonyl chloride separates as an oil and is siphoned off three times during the chlorine addition. The product is dissolved in ether the ethereal solution is washed with water, dried, and distilled. The product boils at 71-72°/20 mm. and is formed in a yield of 110 g. (66%). 

Benzylsulfonyl chloride is prepared in similar manner by the following procedure. A mixture of 76 g. (1.0 mole) of thiourea, 126 g. (1.17 mole) of benzyl alcohol, and 150 ml. of ethanol is refluxed for 30 minutes, the initial exothermic reaction being controlled by external cooling. After the addition of 1 1. of water the mixture is chlorinated as described above. The solid product (155 g.) is removed several times during the chlorination, and the combined product is recrystallized from benzene to give benzylsulfonyl chloride, m.p. 91-92°. 

Folkers, Russell, and Bost, J. Am. Chem. Soc., 63, 3530 (1941), report that the above reactions may give explosive mixtures if the chlorination is prolonged or the mixture allowed to stand after completion of the chlorination. The formation of nitrogen trichloride is proposed as an explanation. In the preparation of ethanesulfonyl chloride from 110 g. of the isothiuronium salt, a 10-hour chlorination period allowed formation of an explosive mixture. 

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Dehydrochlorination of 2-chloro-l -(trifluoromethyl)ethanesulfonyl chloride (3) with potassium fluoride accompanies the exchange of chlorine for fluorine at the sulfonyl group to afford the 3,3,3-trifluoro-2-(fluorosulfonyl)prop-l-ene (4).24... 

TRIM ETHYLSILYLETH AN ESULFONYL CHLORIDE (SES-CI) (Ethanesulfonyl chloride, 2-(trimethylsilyl)-)... 

Trimethylsilyl)ethanesu]fonamides are usually prepared by reaction of the amine with 2-(trimethy]silyl)ethanesulfonyl chloride in the presence of a suitable base. An improved large scale preparation of this reagent has been published in Organic Syntheses [Scheme 8.142] 319 In the first step sodium bisulfite is added to trimethyivinyJsilane in the presence of the catalytic amount of ten-butyl perbenzoate. The resulting crude sodium sulfonate is then treated with... 

The chiral nitridomanganese complex 545 represents a novel self-contained asymmetric nitrogen-transfer reagent which has been used to convert alkenes to scalemic aziridines directly, although a stoichiometric amount of transfer reagent is required. This protocol makes use of A -2-(trimethylsilyl)ethanesulfonyl chloride (SESCl) (546) as an activator, providing A -SES-aziridines 547 that are easily deprotected under mild conditions using... 

CjHsClOjS, Ethanesulfonyl chloride.. 141 CjHsClS, -Chloroethyl mercaptan... 78... 

The oxidation of mercaptans with chlorine in water gives sulfonyl chlorides. Ethyl mercaptan and pentyl mercaptan afford ethanesulfonyl chloride and pentanesulfonyl chloride in yields of 73 and 78% at 5 and 1-5 C, respectively [6S3]. 

Loev and Kormendy147 first synthesized a 2,1-benzothiazine 2,2-dioxide by converting 2-(o-nitrophenyl)ethanesulfonyl chloride to the sulfonate salt 221 which was catalytically reduced to the amine 222. Treatment of 222 with phosphorus pentachloride/acetyl chloride afforded 3,4-dihydro-1//-2,1-benzothiazine 2,2-dioxide (223). They also prepared 4-phenyl-3,4-dihydro-IH-2,1-benzothiazine 2,2-dioxide (225) by treating styrene sulfonanilide (224 R = Ph) with polyphosphoric acid. However, they were unable to cyclize the ethylene sulfonamide (224 R = H) to 223 using this route.147... 

Figure 4. pH-product ratio (14 11) profile for the hydrolysis of 2-hydroxy-ethanesulfonyl chloride (IX) in the presence of NaCl (1 M) at 25.0 °C. 

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