trichloromethanethiol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml flask equipped with a stirrer and thermomether was charged with 5.0 g (0.03 mol) of 1,2,3-benzoxthiazin-4-(3H)-one 2-oxide, 5.3 g (0.03 mol) of perchloromethyl mercaptan, 3.1 g (0.03 mol) of thiethylamine and 150 ml of methylene chloride. The resulting mixture was stirred at ambient temperature for 1 hour. At the end of this time, the reaction mixture was filtered and washed 3 times with equal amounts of water. After drying, the solvent was removed by evaporation. The crude product was passed through a 250-g silica-gel column using hexane, 10% ether/hexane, and 20% ether/hexane, respectively. Evaporation gave 4 g of 3-(trichloromethylthio)-1,2,3-benzoxathiazin-4-(3H)-one 2-oxide having a melting point of 65°-67° C. A 300-ml flask equipped with a stirrer At the end of this time, the reaction mixture was filtered washed 3 times with equal amounts of water After drying the solvent was removed by evaporation Evaporation

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Perchloromethylmercaptan (5.6 g, 0.03 mol) and 2-fluoro-2,2-dinitroethanol (5.0 g, 0.033 mol) in 30 ml of methylene chloride was combined with 0.3 g of tetrabutyl ammonium chloride in 20 ml of water and the vigorously stirred mixture was cooled in an ice-salt bath. A solution obtained by diluting 2.6 g of 50 percent aqueous sodium hydroxide with 3 ml of water was added dropwise keeping the temperature at 0° C. Separation of the methylene chloride layer and removal of the solvent gave 8.2 g of an oil which was extracted with 2×40 ml of hexane. The combined extracts were passed through a silica gel 60 pad and the pad was washed with benzene. Removal of solvent gave 5.9 g (65 percent) of an oil which was essentially pure by TLC and GLC analysis; H-NMR (CDCl3): δ 5.37 (d); mass spectrum (C.I.): m/e 304, 302, 267, 269. the vigorously stirred mixture was cooled in an ice-salt bath A solution obtained was added dropwise at 0° C Separation of the methylene chloride layer and removal of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Perchloromethylmercaptan (5.6 g, 0.03 mol) and 2-fluoro-2,2-dinitroethanol (5.0 g, 0.033 mol) in 30 ml of methylene chloride was combined with 0.3 g of tetrabutyl ammonium chloride in 20 ml of water and the vigorously stirred mixture was cooled in an ice-salt bath. A solution obtained by diluting 2.6 g of 50 percent aqueous sodium hydroxide with 3 ml of water was added dropwise keeping the temperature at 0° C. Separation of the methylene chloride layer and removal of the solvent gave 8.2 g of an oil which was extracted with 2×40 ml of hexane. The combined extracts were passed through a silica gel 60 pad and the pad was washed with benzene. Removal of solvent gave 5.9 g (65 percent) of an oil which was essentially pure by TLC and GLC analysis; H-NMR (CDCl3): δ 5.37 (d); mass spectrum (C.I.): m/e 304, 302, 267, 269. the vigorously stirred mixture was cooled in an ice-salt bath A solution obtained was added dropwise at 0° C Separation of the methylene chloride layer and removal of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 75.6 gm of sodium hydroxide in 100 ml of water was added to a stirred mixture of 101.4 gm of p-nitrobenzamidine hydrochloride, 70 gm of perchloromethyl mercaptan and 760 ml of dichloromethane, while keeping the temperature below -5° C. After additional 2 hours at -5° C., the resulting suspension was filtered, and the organic phase was separated, evaporated to dryness, and the residual solid was recrystallized from 95% ethanol, yielding 45 gm of the title compound, m.p. 143°-145° C. the temperature below -5° C the resulting suspension was filtered the organic phase was separated evaporated to dryness the residual solid was recrystallized from 95% ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an ice-cooled solution of 2-(3-chlorophenyl)-2-(tetrahydropyran-2-yloxy)acetamidine hydrochloride (12.0 g, 39.51 mmol) in dichloromethane (20 mL) and sodium hydroxide (9.49 g, 0.237 mol, dissolved in 60 mL water) was added a solution of perchloromethyl mercaptan (9.18 g, 49.46 mmol) in dichloromethane (50 mL) over a period of 35 min. The reaction mixture was stirred at ice-cold temperature for a further 1 h and the organic layer was collected, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by column chromatography on silica gel using a mixture of hexane and ethyl acetate (94/6) afforded the title compound as a light yellow oil (8.4 g, 61.5%). 1H-NMR (CDCl3) δ7.56 (d, J=6.9 Hz, 1H, Ar--H), 7.39-7.44 (m, 1H, Ar--H), 7.28-7.32 (m, 2H, Ar--H),6.08 and 6.03 (s, 0.5H each, α-H), 4.84 and 4.72 (t, J=3.1Hz, 0.5H each, OCHO), 3.49-3.92 (m, 2H, OCH2), 1.55-1.94 (m, 6H, 3CH2). the organic layer was collected dried (sodium sulfate) filtered concentrated in vacuo Purification by column chromatography on silica gel using a mixture of hexane and ethyl acetate (94/6)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an ice-cooled solution of 2-(3-chlorophenyl)-2-(tetrahydropyran-2-yloxy)acetamidine hydrochloride (12.0 g, 39.51 mmol) in dichloromethane (20 mL) and sodium hydroxide (9.49 g, 0.237 mol, dissolved in 60 mL water) was added a solution of perchloromethyl mercaptan (9.18 g, 49.46 mmol) in dichloromethane (50 mL) over a period of 35 min. The reaction mixture was stirred at ice-cold temperature for a further 1 h and the organic layer was collected, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by column chromatography on silica gel using a mixture of hexane and ethyl acetate (94/6) afforded the title compound as a light yellow oil (8.4 g, 61.5%). 1H-NMR (CDCl3) δ7.56 (d, J=6.9 Hz, 1H, Ar--H), 7.39-7.44 (m, 1H, Ar--H), 7.28-7.32 (m, 2H, Ar--H),6.08 and 6.03 (s, 0.5H each, α-H), 4.84 and 4.72 (t, J=3.1Hz, 0.5H each, OCHO), 3.49-3.92 (m, 2H, OCH2), 1.55-1.94 (m, 6H, 3CH2). the organic layer was collected dried (sodium sulfate) filtered concentrated in vacuo Purification by column chromatography on silica gel using a mixture of hexane and ethyl acetate (94/6)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into the mixture of 20 ml of toluene and 10 ml of water were added 2.53 g of 4-methoxybenzylisothiourea hydrogen chloride, 2.03 g of perchloromethyl mercaptan, and 50 mg of benzyltriethylammonium chloride, and a solution of 1.74 g of sodium hydroxide in 10 ml of water was added dropwise to the mixture at about 0° C. over 4 hours. After the addition, the mixture was stirred for 1 hour at room temperature. Into the reaction mixture was added t-butyl methyl ether, and extracted. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the residue obtained was subjected to silica gel column chromatography to give 5.38 g of 5-chloro-3-(4-methoxybenzyl)thio-1,2,4-thiadiazole. After the addition extracted The organic layer was dried over anhydrous sodium sulfate concentrated the residue obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into the mixture of 20 ml of toluene and 10 ml of water were added 2.53 g of 4-methoxybenzylisothiourea hydrogen chloride, 2.03 g of perchloromethyl mercaptan, and 50 mg of benzyltriethylammonium chloride, and a solution of 1.74 g of sodium hydroxide in 10 ml of water was added dropwise to the mixture at about 0° C. over 4 hours. After the addition, the mixture was stirred for 1 hour at room temperature. Into the reaction mixture was added t-butyl methyl ether, and extracted. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the residue obtained was subjected to silica gel column chromatography to give 5.38 g of 5-chloro-3-(4-methoxybenzyl)thio-1,2,4-thiadiazole. After the addition extracted The organic layer was dried over anhydrous sodium sulfate concentrated the residue obtained