[isothiocyanato(phenyl)methyl]benzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzhydryl-isothiocyanate (13.75 g), N-methyl aminooxy acetic acid hydrochloride (8.6 g), triethylamine (16 g) and chloroform (200 mL) was heated at reflux for three hours, stirred at ambient temperature for one hour. The mixture was diluted with chloroform (200 mL) and washed with 2N HCl (2×300 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness to give a solid. The solid was stirred in ether (200 mL) and filtered to give 18.8 g of [[[[(benzhydryl)amino]thioxomethyl]methylamino]oxy]acetic acid as a white solid, m.p. 160-162° C. Mass spectrum (−FAB, [M−H]−) m/z 329. 1H-NMR (DMSO-d6; 400 MHz) δ13.55 (br s, 1H), 9.75 (d, 1H), 7.35-7.23 (m, 10H), 6.63 (d, 1H), 4.63 (s, 2H), and 3.42 ppm (s, 3H). was heated at reflux for three hours washed with 2N HCl (2×300 mL) The organic phase was dried over anhydrous magnesium sulfate evaporated to dryness to give a solid filtered

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 13.50 g (0.06 Mole) of benzhydrylisothiocyanate in ether is saturated with anhydrous methylamine in an ice bath. The crystals are filtered to yield the product, N-benzhydryl-N'-methylthiourea; mp 152°-154° C, which is sufficiently pure for the next step. The crystals are filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared by the procedure described in Example 1 using 11.25 g of benzhydryl-isothiocyanate, 7.68 g of sarcosine ethyl ester hydrochloride, 12 g of triethyl amine, and 200 mL of chloroform. The title compound was obtained (7.40 g) as an off-white solid, m.p. 139°-141° C. Anal. Calcd. for C17H16N2O S: C, 68.89; H, 5.44; N, 9.45. Found: C, 68.92; H, 5.43; N, 9.58. Mass spectrum (El, M.+) m/z 296. The title compound was prepared by the procedure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared by the procedure described in Example 1 using 11.25 g of benzhydryl-isothiocyanate, 7.68 g of sarcosine ethyl ester hydrochloride, 12 g of triethyl amine, and 200 mL of chloroform. The title compound was obtained (7.40 g) as an off-white solid, m.p. 139°-141° C. Anal. Calcd. for C17H16N2O S: C, 68.89; H, 5.44; N, 9.45. Found: C, 68.92; H, 5.43; N, 9.58. Mass spectrum (El, M.+) m/z 296. The title compound was prepared by the procedure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Potassium diphenylmethyldithiocarbamate was prepared from diphenylmethyl isothiocyanate and potassium hydrosulfide in a t-butyl alcohol acetone mixture. A mixture of 29.7 g. of this salt, 26.1 g. of methylene bromide, and 10.1 g. of triethylamine in 200 ml. of dimethylformamide was stirred for about one hour keeping the initial reaction temperature below 30° C. by cooling. The mixture was poured into ice-water, partitioned into ethylene chloride, and gave 24.0 g. of crude product upon evaporation of the ethylene chloride. Purification by dry column chromatography on silica gel using 20% methylene chloride in hexane for developing gave 5.5 g. of solids which were recrystallized from isopropyl alcohol to give 4.4 g. of white crystals, m.p. 106.5°-107.5° C. A mixture of 29.7 g reaction temperature below 30° C. by cooling partitioned into ethylene chloride gave 24.0 g of crude product upon evaporation of the ethylene chloride Purification by dry column chromatography on silica gel using 20% methylene chloride in hexane for developing gave 5.5 g of solids which were recrystallized from isopropyl alcohol to give 4.4 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzhydryl-isothiocyanate (13.75 g), N-methyl aminooxy acetic acid hydrochloride (8.6 g), triethylamine (16 g) and chloroform (200 mL) was heated at reflux for three hours, stirred at ambient temperature for one hour. The mixture was diluted with chloroform (200 mL) and washed with 2N HCl (2×300 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness to give a solid. The solid was stirred in ether (200 mL) and filtered to give 18.8 g of [[[[(benzhydryl)amino]thioxomethyl]methylamino]oxy]acetic acid as a white solid, m.p. 160-162° C. Mass spectrum (−FAB, [M−H]−) m/z 329. 1H-NMR (DMSO-d6; 400 MHz) δ13.55 (br s, 1H), 9.75 (d, 1H), 7.35-7.23 (m, 10H), 6.63 (d, 1H), 4.63 (s, 2H), and 3.42 ppm (s, 3H). was heated at reflux for three hours washed with 2N HCl (2×300 mL) The organic phase was dried over anhydrous magnesium sulfate evaporated to dryness to give a solid filtered

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Potassium diphenylmethyldithiocarbamate was prepared from diphenylmethyl isothiocyanate and potassium hydrosulfide in a t-butyl alcohol acetone mixture. A mixture of 29.7 g. of this salt, 26.1 g. of methylene bromide, and 10.1 g. of triethylamine in 200 ml. of dimethylformamide was stirred for about one hour keeping the initial reaction temperature below 30° C. by cooling. The mixture was poured into ice-water, partitioned into ethylene chloride, and gave 24.0 g. of crude product upon evaporation of the ethylene chloride. Purification by dry column chromatography on silica gel using 20% methylene chloride in hexane for developing gave 5.5 g. of solids which were recrystallized from isopropyl alcohol to give 4.4 g. of white crystals, m.p. 106.5°-107.5° C. A mixture of 29.7 g reaction temperature below 30° C. by cooling partitioned into ethylene chloride gave 24.0 g of crude product upon evaporation of the ethylene chloride Purification by dry column chromatography on silica gel using 20% methylene chloride in hexane for developing gave 5.5 g of solids which were recrystallized from isopropyl alcohol to give 4.4 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of sarcosine ethyl ester hydrochloride (7.68 g), benzhydryl-isothiocyanate (11.25 g), triethyl amine (12 g) and chloroform (200 mL) was heated at reflux for 5 hours. The mixture was cooled to ambient temperature, washed with 1N HCl (2×200 mL), then with water (200 mL) The organic phase was evaporated to dryness. The residue was crystallized from ethanol to give the title compound (7.40 g) as an off-white solid, m.p. 139°-141° C. Anal. Calcd. for C17H16N2O S: C, 68.89; H, 5.44; N, 9.45. Found: C, 68.92; H, 5.43; N, 9.58. Mass spectrum (EI, M.+) m/z 296. was heated at reflux for 5 hours washed with 1N HCl (2×200 mL) with water (200 mL) The organic phase was evaporated to dryness The residue was crystallized from ethanol