Thionyl dichloride

Another method for the chlorides involves refluxing the hydrated chlorides with thionyl dichloride (SOCI2) for a few hours an advantage of this method is that the other reaction products are gaseous SO2 and HCl. 

Sc(THF)3Cl3 is a very useful synthon (starting material) for other scandium compounds. It can conveniently be prepared using thionyl dichloride as a dehydrating agent ... 

SYNS SULFINYL CHLORIDE SULFUR CHLORIDE OXIDE SULFUROUS DICHLORIDE SULFUROUS O-XYCHLORIDE THIONYL DICHLORIDE... 

The thiazyl dichloride ion, NSCI2 , has recently been reported. This ion is isoelectronic with thionyl dichloride, OSCI2. 

SOCl2 = [SC120] thionyl dichloride, or sulfur dichloride oxide sulfurous dichloride dichloridooxidosulfur... 

Thionyl dichloride, SOCI2 (prepared, for example, by reaction 16.68 or 16.71), and sulfuryl dichloride, SO2CI2 (prepared by reaction 16.72) are colourless, fuming liquids SOCI2, bp 351K SO2CI2, bp 342 K. Their ease of hydrolysis by water accounts for their fuming nature, e.g. equation 16.73. 

Both SOCI2 and SO2CI2 are available commercially. Thionyl dichloride is used to prepare acyl chlorides (equation 16.74) and anhydrous metal chlorides (i.e. removing tvater of crystallization by reaction 16.73), tvhile SO2CI2 is a chlorinating agent. 

Synonyms Sulfinyl chloride Sulfur chloride oxide Sulfurous dichloride Sulfurous oxychloride Sulfur oxychloride Thionyl dichloride... 

Thionyl dichloride. See Thionyl chloride Thiooctanoic acid. See Thioctic acid Thioperoxydicarbonic acid, dibutyl ester. See Dibutyl xanthogen disulfide Thioperoxydicarbonic acid diethyl ester. See Diethyl xanthogen disulfide Thioperoxydicarbonic diamide, tetrakis (2-methylpropyl)-. See Tetraisobutylthiuram disulfide... 

SULPHUR DICHLORIDE OXIDE, THIONYL CHLORIDE, SOClj... 

Sulphur dichloride oxide (thionyl chloride) on the hydrated chloride can also be used to produce the anhydrous chloride in certain cases, for example copper(II) chloride and chromium(III) chloride ... 

The dichlorides of aliphatic glycols are obtained by reaction with thionyl chloride in the presence of a small quantity of pyridine, for example ... 

Boon has observed that when 2,4-dimethyl-5-thiazolecarboxylic acid (22) is heated with an excess of thionyl chloride, the main product (76%) is 4-methyl-2,5-thiazoledicarboxylic acid dichloride (23) (Scheme 14 (7). 

Reaction with Sulfur Electrophiles. Bisa2iridine compounds can be prepared from sulfur dichloride, thionyl chloride, or sulfuryl chloride... 

Sulfur dichloride is oxidized by sulfur trioxide or chlorosulfuric acid [7790-94-5] (qv) to form thionyl chloride ... 

At present, thionyl chloride is produced commercially by the continuous reaction of sulfur dioxide (or sulfur trioxide) with sulfur monochloride (or sulfur dichloride) mixed with excess chlorine. The reaction is conducted in the gaseous phase at elevated temperature over activated carbon (178). Unreacted sulfur dioxide is mixed with the stoichiometric amount of chlorine and allowed to react at low temperature over activated carbon to form sulfuryl chloride, which is fed back to the main thionyl chloride reactor. 

A number of processes have been devised for purifying thionyl chloride. A recommended laboratory method involves distillation from quinoline and boiled linseed oil. Commercial processes involve adding various high boiling olefins such as styrene (qv) to react with the sulfur chlorides to form adducts that remain in the distillation residue when the thionyl chloride is redistilled (179). Alternatively, sulfur can be fed into the top of the distillation column to react with the sulfur dichloride (180). Commercial thionyl chloride has a purity of 98—99.6% minimum, having sulfur dioxide, sulfur chlorides, and sulfuryl chloride as possible impurities. These can be determined by gas chromatography (181). 

Qindamycin, 7(5)-7-chloro-7-deoxyliQcomycin [18323-44-9] (1, R = H, R = Q), also known as Cleocin, first resulted from the reaction of lincomycin and thionyl chloride (54) improved synthetic methods involve the reaction of lincomycin and triphenylphosphine dichloride or triphenylphosphine in carbon tetrachloride (55). Clindamycin is significantly more active than lincomycin against gram-positive bacteria in vitro, and is absorbed rapidly following oral adnainistration. Clindamycin 2-palmitate [36688-78-5], (6, R = R = OC(CH2) 4CH2), 2-palmitate ester of clindamycin, is... 

The 1,5-isomers 13.3 (E = S) are colourless, air-stable solids. They are prepared by the cyclocondensation reaction of R2PN2(SiMe3)3 with sulfur dichloride or thionyl chloride. A similar cyclocondensation process, using a mixture of SeCU and Sc2Cl2 as a source of selenium, produces a mixture of the isomers 13.2 and 13.3 (E = Se, R = Ph). The structures of 13.3 (E = S, R = alkyl, aryl) are folded eight-membered rings with a cross-ring S S distance of ca. 2.50 This structural... 

In contact with aluminium, disulphur dichloride provokes the instantaneous ignition of the metal. Lithium batteries contain thionyl chloride. A large number of explosions of batteries have been explained by the violent interaction of lithium with the chloride, which was assumed to be reieased through the anode. Sodium combusts in contact with thionyl chloride vapour heated to a temperature of 300°C. Finally, sulphur dichloride gives rise to explosive mixtures on impact with sodium. 

Malonyl dichloride has been prepared from malonic acid and thionyl chloride,4-9 and from carbon suboxide and anhydrous liquid hydrogen chloride.10 This procedure is based on that of Staudinger and Bereza 6 and of Backer and Homan.8... 

In absence of diluent or other effective control of reaction rate, the sulfoxide reacts violently or explosively with the following acetyl chloride, benzenesul-fonyl chloride, cyanuric chloride, phosphorus trichloride, phosphoryl chloride, tetrachlorosilane, sulfur dichloride, disulfur dichloride, sulfuryl chloride or thionyl chloride [1], These violent reactions are explained in terms of exothermic polymerisation of formaldehyde produced under a variety of conditions by interaction of the sulfoxide with reactive halides, acidic or basic reagents [2], Oxalyl chloride reacts explosively with DMSO at ambient temperature, but controllably in dichloromethane at -60°C [3]. 

Preparation of the acetylenic dichloride by conversion of the diol in pyridine with neat thionyl chloride is difficult to control, and hazardous on a large scale. Use of dichloromethane as diluent and operation at —30°C renders the preparation reproducible and safer [1], During distillation at up to 110°C/7-8 mbar, slight overheating of the residue to 120°C caused explosive decomposition [2], Sensitive to detonator, sometimes to mechanical shock [3],... 

Synthesis of dithieno[2,3-A2,3-,7]thiophene derivatives 122 has been accomplished through the Heck reaction of 3-(4-bromo-2-thienyl)acrylic acid 302 to afford 3-(2,4-thienylene)diacrylic acid 303 which was cyclized with thionyl chloride and a catalytic amount of pyridine to the dichloride 120 in 75% yield (Scheme 56) <2005MOL279>. 

Yet other processes have used sulphuryl chloride (S02C12), thionyl chloride (SOCl2) or sulphur dichloride (SC12) as chlorinating agents. 

---