二氯一氟甲烷次硫酰氯

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of 2-methoxy-3-cyano-5-methylpyrrole (0.5 g) in 5 ml of CH2Cl2 was treated with Cl2FCSCl (0.45 ml) and stirred at room temperature for 14 h. The resulting precipitate was filtered, washed with CH2Cl2, and dried under high vacuum to afford an off-white solid (0.59 g), m.p. 175° C. The resulting precipitate was filtered washed with CH2Cl2 dried under high vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of 2-methoxy-3-cyano-5-methylpyrrole (0.5 g) in 5 ml of CH2Cl2 was treated with Cl2FCSCl (0.45 ml) and stirred at room temperature for 14 h. The resulting precipitate was filtered, washed with CH2Cl2, and dried under high vacuum to afford an off-white solid (0.59 g), m.p. 175° C. The resulting precipitate was filtered washed with CH2Cl2 dried under high vacuum

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cooled (0° C.) solution of 3.00 g (9.74 mmoles) of the 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethylpyrrole prepared above in 60 mL of dichloromethane was added dropwise 1.03 mL (1.67 g, 9.86 mmoles) of dichlorofluoromethanesulfenyl chloride in 5 mL of dichloromethane solution. The mixture was maintained at 0° C. for 3 hours and then washed with a saturated aqueous solution of NaHCO3. Removal of solvent under reduced pressure afforded a black oil which was chromatographed on silica gel with a 1% EtOAc in hexane eluent to give 3.85 g (90%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethyl-3-(dichlorofluoromethylthio)pyrrole as a yellow oil: 1H NMR (CDCl3): δ2.00 (s, 3H), 2.10 (s, 3H), 6.27 (s, 1H), 7.80 (s, 2H). washed with a saturated aqueous solution of NaHCO3 Removal of solvent under reduced pressure afforded a black oil which was chromatographed on silica gel with a 1% EtOAc in hexane eluent

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cooled (0° C.) solution of 3.00 g (9.74 mmoles) of the 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethylpyrrole prepared above in 60 mL of dichloromethane was added dropwise 1.03 mL (1.67 g, 9.86 mmoles) of dichlorofluoromethanesulfenyl chloride in 5 mL of dichloromethane solution. The mixture was maintained at 0° C. for 3 hours and then washed with a saturated aqueous solution of NaHCO3. Removal of solvent under reduced pressure afforded a black off which was chromatographed on silica gel with a 1% EtOAc in hexane eluent to give 3.85 g (90%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethyl-3-(dichlorofluoromethylthio)pyrrole as a yellow off: 1H NMR (CDCl3): δ2.00 (s, 3H), 2.10 (s, 3H), 6.27 (s, 1H), 7.80 (s, 2H). washed with a saturated aqueous solution of NaHCO3 Removal of solvent under reduced pressure afforded a black off which was chromatographed on silica gel with a 1% EtOAc in hexane eluent

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The sodium salt of 5-cyano-1-phenyluracil is reacted with each of dichlorofluoromethanesulfenyl chloride and trichloromethanesulfenyl chloride following the procedure of Example 1 to yield 5-cyano-3-dichlorofluoromethanesulfenyl-1-phenyluracil and 5-cyano-3-trichloromethanesulfenyl-1-phenyluracil, respectively.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 20.4 g of fluorodichloromethanesulphenyl chloride is added dropwise at 0° C, with thorough stirring, to 25.9 g of 3-(3',4'-dichlorophenyl)-5-methyl-imidazolidine-2,4-dione in 500 ml of acetic acid ethyl ester, and after 2 hours an addition is made dropwise, likewise at 0° C. of 12.1 g of triethylamine in 100 ml of acetic acid ethyl ester. After the whole has been stirred for 3 hours at room temperature, the triethylamine hydrochloride is filtered off; the solvent is evaporated off from the filtrate and the residue is recrystallised in methanol. Compound No. 2 melts at 138° - 140° C after recrystallisation. after 2 hours an addition the triethylamine hydrochloride is filtered off the solvent is evaporated off from the filtrate the residue is recrystallised in methanol 2 melts at 138° - 140° C after recrystallisation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 23.8 g of fluorodichloromethanesulphenyl chloride in 100 ml of acetic acid ethyl ester is added dropwise within 20 minutes at -10° C, with vigorous stirring, to a suspension of 22.5 g of 3-(3'-chloro-4'-methylphenyl)-imidazolidine-2,4-dione in 400 ml of acetic acid ethyl ester, and after one hour there is also added dropwise, at 0° C in the course of 10 minutes, 14.2 g of triethylamine in 100 ml of acetic acid ethyl ester; the cooling bath is subsequently removed and stirring is continued for 3 hours at room temperature. The triethylamine hydrochloride that has precipitated is filtered off and then washed with 100 ml of acetic acid ethyl ester; the solvent is evaporated off in vacuo to obtain, after recrystallisation in methanol, Compound No. 1 which melts at 166° - 167° C. the cooling bath is subsequently removed The triethylamine hydrochloride that has precipitated is filtered off washed with 100 ml of acetic acid ethyl ester the solvent is evaporated off in vacuo to obtain after recrystallisation in methanol

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The sodium salt of 5-cyano-1-phenyl-uracil is reacted with each of dichlorofluoromethane sulphenyl chloride and trichloromethane sulphenyl chloride following the foregoing procedure to yield 5-cyano-3-dichlorofluoromethane sulphenyl-1-phenyl-uracil and 5-cyano-1-phenyl-3-trichloromethane sulphenyl uracil.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 23.8 g of fluorodichloromethanesulphenyl chloride in 100 ml of acetic acid ethyl ester is added dropwise within 20 minutes at -10°C, with vigorous stirring, to a suspension of 22.5 g of 3-(3'-chloro-4'-methylphenyl)imidazolidine-2,4-dione in 400 ml of acetic acid ethyl ester, and after one hour there is also added dropwise, at 0°C in the course of 10 minutes, 14.2 g of triethylamine in 100 ml of acetic acid ethyl ester; the cooling bath is subsequently removed and stirring is continued for 3 hours at room temperature. The triethylamine hydrochloride that has precipitated is filtered off and then washed with 100 ml of acetic acid ethyl ester; the solvent is evaporated off in vacuo to obtain, after recrystallisation in methanol, Compound No. 1 which melts at 166° - 167°C. the cooling bath is subsequently removed The triethylamine hydrochloride that has precipitated is filtered off washed with 100 ml of acetic acid ethyl ester the solvent is evaporated off in vacuo to obtain after recrystallisation in methanol

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 240 g (2 moles) of acetophenone were dissolved in 300 ml of chloroform and, after addition of 3 ml of ethanol and 109 g (0.64 mole) of fluorodichloromethanesulphenyl chloride, the mixture was heated to the reflux temperature. A further 400 g (2.36 moles) of fluorodichloromethane-sulphenyl chloride were added dropwise in the course of 30 minutes and the mixture was then heated under reflux for 5 hours. For subsequent working up, the reaction mixture was subjected to fractional distillation under reduced pressure. After first runnings of unchanged starting material, 126 g of fluorodichloromethyl-mercaptomethyl phenyl ketone were obtained in the form of a liquid of boiling point 128° C./0.4 mbar. the mixture was heated to the reflux temperature the mixture was then heated under reflux for 5 hours the reaction mixture was subjected to fractional distillation under reduced pressure