1,3,5-trichloro-2-isothiocyanatobenzene

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

Procedure: 2,4,6-Trichlorophenyl isothiocyanate was reacted with 2-butylamine followed by chloroacetic acid according to Method C8a to afford 2-(2,4,6-trichlorophenylimino)-3-(2-butyl)-1,3-thiazolidin-4-one.

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

Procedure: 2,4,6-Trichlorophenyl isothiocyanate was reacted with 2-butylamine followed by chloroacetic acid according to Method C8a to afford 2-(2,4,6-trichlorophenylimino)-3-(2-butyl)-1,3-thiazolidin-4-one.

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

Procedure: 2,4,6-Trichlorophenyl isothiocyanate was reacted with 2-butylamine followed by chloroacetic acid according to Method C8a to afford 2-(2,4,6-trichlorophenylimino)-3-(2-butyl)-1,3-thiazolidin-4-one.

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

Procedure: A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (200 mg, 0.773 mmol) and 2,4,6-trichlorophenyl isothiocyanate (406 mg, 1.70 mmol) was stirred at room temperature for 2 days and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture to give the title compound as a red oil (285 mg, 0.574 mmol, 74%). concentrated in vacuo The residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture

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

Procedure: A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (200 mg, 0.773 mmol) and 2,4,6-trichlorophenyl isothiocyanate (406 mg, 1.70 mmol) was stirred at room temperature for 2 days and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture to give the title compound as a red oil (285 mg, 0.574 mmol, 74%). concentrated in vacuo The residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 5 ml dimethylformamide solution of 3.7 g ethyl 3-amino-4,4,4-trifluorocrotonate was added dropwise to a 30 ml dimethylformamide solution of 1.0 g of sodium hydride (purity: 55%) with stirring at 5° C. The mixed solution was stirred at room temperature for 15 minutes, then cooled to 5° C. and added dropwise with a 10 ml dimethylformamide solution of 5.0 g of 2,4,6-trichlorophenyl isothiocyanate. The resulting solution was heated to room temperature and further stirred at 130° C. for 2 hours. Then the solvent was distilled away under reduced pressure and the residue was dissolved by adding 200 ml of water and washed with diethyl ether. The obtained aqueous layer was added into a mixed solution of 30 ml of concentrated hydrochloric acid and 100 g of ice and extracted with 200 ml of ethyl acetate. The obtained organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 2.8 g of a crude product. This product was purified by preparative thin-layer chromatography (developing solvent: a mixed solvent of chloroform and ethyl acetate) to obtain 0.43 g of the objective compound. The mixed solution was stirred at room temperature for 15 minutes cooled to 5° C. The resulting solution was heated to room temperature further stirred at 130° C. for 2 hours Then the solvent was distilled away under reduced pressure the residue was dissolved by adding 200 ml of water washed with diethyl ether The obtained aqueous layer was added into a mixed solution of 30 ml of concentrated hydrochloric acid and 100 g of ice extracted with 200 ml of ethyl acetate The obtained organic layer was washed with a sodium chloride aqueous solution dried over anhydrous sodium sulfate Then the solvent was distilled away under reduced pressure to obtain 2.8 g of a crude product This product was purified by preparative thin-layer chromatography (

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

Procedure: 2,4,6-Trichlorophenyl isothiocyanate was reacted with 2-butylamine followed by chloroacetic acid according to Method C8a to afford 2-(2,4,6-trichlorophenylimino)-3-(2-butyl)-1,3-thiazolidin-4-one.