1-amino-3-butylthiourea

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

実験手順: A mixture of 5.9 g (0.04 mole) of 4-butyl-3-thiosemicarbazide, 3.3 ml (0.04 mole) of 37% hydrochloric acid and 10.5 g (0.04 mole) of methyl 3-(4-chlorobenzoyl)-3-chloropropionate in 150 ml of 1-butanol was stirred at ambient temperature for 4 hours and heated at reflux for 40 hours. The reaction mixture was diluted with 50 ml of water, filtered to remove the inorganic sulfur, then concentrated in vacuo (19 g). The residue was placed on a 400 g Florisil column and eluted with benzene then with an acetone:benzene gradient (0.5 to 10%). The product fractions were combined and concentrated in vacuo to give 15.2 g of pale yellow solid. Recrystallization from 2-propanol yielded 2 g (14%) of fluffy white crystals, mp 130°-130.5° C. heated at reflux for 40 hours filtered to remove the inorganic sulfur concentrated in vacuo (19 g) eluted with benzene concentrated in vacuo

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

実験手順: 4.47 g of 2,4-dichlorophenacyl chloride and 2.66 g of 4-n-butyl-thiosemicarbazide are reacted under the conditions of Example 2 in 150 ml of methanol. The solid obtained is recrystallized from methanol/ethyl acetate, producing 3.98 g of N-butyl-5-(2,4-dichlorophenyl)-6H-1,3,4-thiadiazin-2-amine monohydrochloride. m.p. 180°-182° C. The solid obtained is recrystallized from methanol/ethyl acetate

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

実験手順: A mixture of 5.9 g (0.04 mole) of 4-butyl-3-thiosemicarbazide, 3.3 ml (0.04 mole) of 37% hydrochloric acid and 10.5 g (0.04 mole) of methyl 3-(4-chlorobenzoyl)-3-chloropropionate in 150 ml of 1-butanol was stirred at ambient temperature for 4 hours and heated at reflux for 40 hours. The reaction mixture was diluted with 50 ml of water, filtered to remove the inorganic sulfur, then concentrated in vacuo (19 g). The residue was placed on a 400 g Florisil column and eluted with benzene then with an acetone:benzene gradient (0.5 to 10%). The product fractions were combined and concentrated in vacuo to give 15.2 g of pale yellow solid. Recrystallization from 2-propanol yielded 2 g (14%) of fluffy white crystals, mp 130°-130.5° C. heated at reflux for 40 hours filtered to remove the inorganic sulfur concentrated in vacuo (19 g) eluted with benzene concentrated in vacuo

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

実験手順: A mixture of 5.9 g (0.04 mole) of 4-butyl-3-thiosemicarbazide, 3.3 ml (0.04 mole) of 37% hydrochloric acid and 10.5 g (0.04 mole) of methyl 3-(4-chlorobenzoyl)-3-chloropropionate in 150 ml of 1-butanol was stirred at ambient temperature for 4 hours and heated at reflux for 40 hours. The reaction mixture was diluted with 50 ml of water, filtered to remove the inorganic sulfur, then concentrated in vacuo (19 g). The residue was placed on a 400 g Florisil column and eluted with benzene then with an acetone:benzene gradient (0.5 to 10%). The product fractions were combined and concentrated in vacuo to give 15.2 g of pale yellow solid. Recrystallization from 2-propanol yielded 2 g (14%) of fluffy white crystals, mp 130°-130.5° C. heated at reflux for 40 hours filtered to remove the inorganic sulfur concentrated in vacuo (19 g) eluted with benzene concentrated in vacuo

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

実験手順: 4-n-Butylthiosemicarbazide (20.0 g. or 0.136 mole) was heated to reflux with a solution of methanol (100 ml.), sodium methoxide (7.55 g. or 0.140 mole) and ethyl formate (20.7 g. or 0.280 mole). After 8 and 16 hours, 10 ml. and 5 ml. of ethyl formate was added to the refluxing solution. After 24 hours total reflux, the solvent was removed under reduced pressure and the residue was dissolved in water (100 ml.). The pH of the solution was adjusted to about 12 with 50% sodium hydroxide solution. This solution was then heated on a steam bath for 45 minutes, cooled and acidified with dilute hydrochloric acid. The resulting oil was extracted into ether. The ether was dried over sodium sulphate and removed under vacuum. The resulting oil was crystallized from ether-hexane to give 11.8 g. (55% yield) of 3-mercapto-4-n-butyl 1,2,4-triazole, m.p. 67°-69° C. The structure was confirmed by its nuclear magnetic resonance spectrum and its mass spectrum. After 8 and 16 hours, 10 ml the solvent was removed under reduced pressure the residue was dissolved in water (100 ml.) This solution was then heated on a steam bath for 45 minutes cooled The resulting oil was extracted into ether The ether was dried over sodium sulphate removed under vacuum The resulting oil was crystallized from ether-hexane to give 11.8 g

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

実験手順: 4-n-Butylthiosemicarbazide (20.0 g. or 0.136 mole) was heated to reflux with a solution of methanol (100 ml.), sodium methoxide (7.55 g. or 0.140 mole) and ethyl formate (20.7 g. or 0.280 mole). After 8 and 16 hours, 10 ml. and 5 ml. of ethyl formate was added to the refluxing solution. After 24 hours total reflux, the solvent was removed under reduced pressure and the residue was dissolved in water (100 ml.). The pH of the solution was adjusted to about 12 with 50% sodium hydroxide solution. This solution was then heated on a steam bath for 45 minutes, cooled and acidified with dilute hydrochloric acid. The resulting oil was extracted into ether. The ether was dried over sodium sulphate and removed under vacuum. The resulting oil was crystallized from ether-hexane to give 11.8 g. (55% yield) of 3-mercapto-4-n-butyl-1,2,4-triazole, m.p. 67°-69° C. The structure was confirmed by its nuclear magnetic resonance spectrum and its mass spectrum. After 8 and 16 hours, 10 ml the solvent was removed under reduced pressure the residue was dissolved in water (100 ml.) This solution was then heated on a steam bath for 45 minutes cooled The resulting oil was extracted into ether The ether was dried over sodium sulphate removed under vacuum The resulting oil was crystallized from ether-hexane to give 11.8 g

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

実験手順: 4.47 g of 2,4-dichlorophenacyl chloride and 2.66 g of 4-n-butyl-thiosemicarbazide are reacted under the conditions of Example 2 in 150 ml of methanol. The solid obtained is recrystallized from methanol/ethyl acetate, producing 3.98 g of N-butyl-5-(2,4-dichlorophenyl)-6H-1,3,4-thiadiazin-2-amine monohydrochloride. m.p. 180°-182° C. The solid obtained is recrystallized from methanol/ethyl acetate

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

実験手順: A mixture of 5.9 g (0.04 mole) of 4-butyl-3-thiosemicarbazide, 3.3 ml (0.04 mole) of 37% hydrochloric acid and 10.5 g (0.04 mole) of methyl 3-(4-chlorobenzoyl)-3-chloropropionate in 150 ml of 1-butanol was stirred at ambient temperature for 4 hours and heated at reflux for 40 hours. The reaction mixture was diluted with 50 ml of water, filtered to remove the inorganic sulfur, then concentrated in vacuo (19 g). The residue was placed on a 400 g Florisil column and eluted with benzene then with an acetone:benzene gradient (0.5 to 10%). The product fractions were combined and concentrated in vacuo to give 15.2 g of pale yellow solid. Recrystallization from 2-propanol yielded 2 g (14%) of fluffy white crystals, mp 130°-130.5° C. heated at reflux for 40 hours filtered to remove the inorganic sulfur concentrated in vacuo (19 g) eluted with benzene concentrated in vacuo