5-Benzylthiuronium chloride

To a concentrated solution of 1 g of the add in water or alcohol add a few drops of phenolphthalein, and neutralize with N sodium hydroxide solution. Treat the solution so formed (or a solution of 1 g of the solid sodium or potassium salt) with 2 drops of N hydrochloric acid and add a solution of 2g of 5-benzylthiuronium chloride in 10 ml of water. (The presence of an unpleasant odour at this stage indicates decomposition of the reagent to benzyl mercaptan.) Cool in ice to precipitate the salt, and filter. Recrys-tallization (aqueous alcohol) is sometimes difficult. 

Benzoyl-a-(ethanol)thiourea, B-00129 Benzoyl-AT -(2-pyridyl)thiourea, B-OOl 59 5 -Benzylthiuronium chloride, in B-00193 A/, A -Bis(l,l-dimethylethyl)thiourea, in T-00175... 

Amides (except urea and thiourea), imides and nitriles, after the above alkaline hydrolysis, give derivatives similarly to those from the alkaline solution obtained from ammonium salts (p. 360). (A) If the original compound is aromatic, acidification of the cold solution deposits the crystalline acid. (B) The cold solution, when carefully neutralised (p. 332) and treated with benzylthiuronium chloride, deposits the thiuromum salt. 

SYNS BENZYUSOTHIOURONIUM CHLORIDE 2-BENZYLISOTHIOURONIUM CHLORIDE O BENZYL THIOPSEUDOUREA HYDROCHLORIDE 2-BENZYL-2-THIO-PSEUDOUREA HYDROCHLORIDE BENZYL-THIURONIUM CHLORIDE S-BENZYLTHIURONIUM CHLORIDE BTKH ISOTHIOURONIUM CHLORIDE. BENZYL 2-THIO-2-BENZYL-PSEUDOUREA HYDROCHLORIDE TL944 USAF EK-2124... 

BENZYL-2-THIO-PSEUDOUREA HYDROCHLORIDE see BEU500 BENZYLTHIURONIUM CHLORIDE see BEU500 S-BENZYLTHIURONIUM CHLORIDE see BEU500 BENZYL TRICHLORIDE see BFL250 BENZYL TRIMETHYL AMMONIUM IODIDE see BFM750... 

From the sodium or the potassium salt of the acid and S-benzylthiuronium chloride in water. 

From sodium or potassium sulfonate and S-benzylthiuronium chloride in alcohol See i 1 Donleavy, y Amer Chem 5oc, 58, 1004 (1936)... 

It is advantageous to use S-benzylthiuronium chloride for the preparation of sulfonic acid salts, because this type of salt was prepared from numerous sulfonic acids (38—45). 

Sodium sulfonate (2 — 3 mmole) is dissolved in a minimum amount of water [in case only free sulfonic acid is available, it is dissolved in 1.5 to 2 ml of 10% NaOH and neutralized (with respect to phenolphthalein) with HCl] and mixed with a solution of 250 mg of S-benzylthiuronium chloride in the required amount of water (in the case of disulfonic acid 500 mg of the reagent are used). The solutions are mixed in the cold by adding the sodium sulfonate solution dropwise to the reagent solution with continuous shaking. The separated salt is washed with water and crystallized by dissolving it in a minimum amoimt of boiling ethanol and by adding water dropwise to incipient turbidity. 

Procedure Naphthalenesulfonic acid (100 mg) is dissolved in 2 ml of water and neutralized (with respect to phenolphthalein) with 2 n NaOH. S-Benzylthiuronium chloride (0.15 g) is dissolved in the required amount of hot ethanol, and this solution is added dropwise with continuous shaking to the sulfonic acid salt solution. After 10 min standing in the refrigerator the salt is filtered off under suction and washed with 1 ml of water. Yield, 0.23 g mp, 187—192 °C after crystallization from 3 ml of 70% ethanol, 0.18 g, mp 193 °C. 

Procedure Potassium anthraquinonesulfonate (0.3 g) is heated under continuous shaking with 5 ml of water to complete dissolution, and 0.3 g of S-benzylthiuronium chloride dissolved in 5 ml of water is added in several portions. The mixture is allowed to stand in a refrigerator for 1 hr and the product is filtered off under suction and washed with 5 ml of water. Yield, 0.4 g mp, 208 — 210 °C. Crystallization of this product from 3 ml of 30% aqueous ethanol gives 0.3 g of product, mp 208—210 °C. 

Procedure S-Benzylthiuronium chloride (0.5 g) is refluxed in a 10-ml flask with 5 ml of n NaOH for 30 min. Then 10 ml of the 10% methanolic 2,4-dinitrochlorobenzene solution and 10 ml of methanol are added to the mixture and boiling is continued for another 30 min. The mixture is then filtered while hot through a folded filter, the filtrate is allowed to stand in a refrigerator, and the separated derivative is filtered off under suction using a filtration tube. Yield, 0.17 g the melting point was imsharp. After recrystallization from 6.5 ml of ethanol the product weighed 0.1 g, mp 127 ""C after a second crystallization from 5 ml of ethanol the yield was 60 mg, mp 130 °C. 

Kidwai et al. (2003) synthesized 4,6-diaryl-2-(4-morphohnyl/l-piperidinyl/l-pyrrolidinyl)pyrimidines by nucleophilic substitution reaction of substituted chal-cones, S-benzylthiuronium chloride (SBT) and morpholine/piperidine/pyrrolidine in ethanol. The rate enhancement and high yield was attributed to the coupling of solvent-free conditions and microwaves. 

Benzyl-2-thiopseudourea, B-00193 5-Benzyl-2-thioxo-4-imidazolidinone, B-00194 S-Benzylthiuronium chloride, in B-00193... 

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