1-amino-3-prop-2-enylthiourea

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

Procedure: 3.93 g (0.03 mole) of 4-allyl-thiosemicarbazide and 7.00 g (0.03 mole) of 2,4-dichlorophenacyl chloride are reacted in accordance with the conditions of Example 1. Recrystallization from methanol/methyl acetate produces 8 g of 5-(2,4-dichlorophenyl)-N-2-propenyl-6H-1,3,4-thiadiazin-2-amine. m.p. 188°-189° C. Recrystallization from methanol/methyl acetate

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

Procedure: A mixture of 26.24 g (0.2 mole) of 4-(2-propenyl)-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 150 mL of absolute ethanol was stirred under nitrogen atmosphere for 1.5 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1.5 hr. The reaction mixture was stirred at ambient temperature for ~72 hr, heated to reflux and filtered to remove the amorphous sulfur. The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone to give 29 g of product. Recrystallization from acetone gave 21 g of needle-like crystals tinted with yellow. A second recrystallization from benzene gave 15.8 g of fine white needles, mp 133°-134° C. A rework of the filtrates from both recrystallizations gave an additional 7 g of crude product. heated at reflux for 1.5 hr The reaction mixture was stirred at ambient temperature for ~72 hr heated to reflux filtered to remove the amorphous sulfur The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone

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

Procedure: A mixture of 26.24 g (0.2 mole) of 4-(2-propenyl)-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 150 mL of absolute ethanol was stirred under nitrogen atmosphere for 1.5 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1.5 hr. The reaction mixture was stirred at ambient temperature for ~72 hr, heated to reflux and filtered to remove the amorphous sulfur. The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone to give 29 g of product. Recrystallization from acetone gave 21 g of needle-like crystals tinted with yellow. A second recrystallization from benzene gave 15.8 g of fine white needles, mp 133°-134° C. A rework of the filtrates from both recrystallizations gave an additional 7 g of crude product. heated at reflux for 1.5 hr The reaction mixture was stirred at ambient temperature for ~72 hr heated to reflux filtered to remove the amorphous sulfur The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone

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

Procedure: Analogously to the procedure of Example 1, 5,6,7,7a-tetrahydro-1-(2-propenyl-1H-pyrrolo[1,2-b][1,2,4]triazole-2(3H)-thione, 5,6,7,7a-tetrahydro-1,7a-diphenyl-1H-pyrrolo[1,2-b][1,2,4]triazole-2(3H)-thione, 7a-(4-methylphenyl)-tetrahydro-1-methyl-1H-pyrrolo[1,2-b][1,2,4]triazole-2(3H)-thione are prepared by reacting, respectively, 4-allyl-thiosemicarbazide with 1-phenyl-4-chloro-butan-1-one, 4-phenyl-thiosemicarbazide with 1-phenyl-4-chlorobutan-1-one and 4-methyl-thiosemicarbazide with 1-(4-methylphenyl)-4-chloro-butan-1-one.

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

Procedure: From 4-(2-propenyl)-3-thiosemicarbazide and 1-chloro-3,3-dimethyl-2-butanone.

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

Procedure: From 4-(2-propenyl)-3-thiosemicarbazide and phenacyl chloride.

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

Procedure: A mixture of 26.24 g (0.2 mole) of 4-(2-propenyl)-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 150 mL of absolute ethanol was stirred under nitrogen atmosphere for 1.5 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1.5 hr. The reaction mixture was stirred at ambient temperature for ~72 hr, heated to reflux and filtered to remove the amorphous sulfur. The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone to give 29 g of product. Recrystallization from acetone gave 21 g of needle-like crystals with yellow. A second recrystallization from benzene gave 15.8 g of fine white needles, mp 133°-134° C. A rework of the filtrate from both recrystallizations gave an additional 7 g of crude product. heated at reflux for 1.5 hr The reaction mixture was stirred at ambient temperature for ~72 hr heated to reflux filtered to remove the amorphous sulfur The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone

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

Procedure: From 4-(2-propenyl)-3-thiosemicarbazide and 1-chloro-3,3-dimethyl-2-butanone.

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

Procedure: From 4-(2-propenyl)-3-thiosemicarbazide and phenacyl chloride.

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

Procedure: From 4-(2-propenyl)-3-thiosemicarbazide and chloroacetone.

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

Procedure: 3.93 g (0.03 mole) of 4-allyl-thiosemicarbazide and 7.00 g (0.03 mole) of 2,4-dichlorophenacyl chloride are reacted in accordance with the conditions of Example 1. Recrystallization from methanol/methyl acetate produces 8 g of 5-(2,4-dichlorophenyl)-N-2-propenyl-6H-1,3,4-thiadiazin-2-amine. m.p. 188°-189° C. Recrystallization from methanol/methyl acetate