1,3-dipropylthiourea

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 6.8 of 2-bromo-4'-chloro-3'-dimethylsulfamoylacetophenone were reacted according to Example 23 with 3.3 g of 1,3-dipropylthiourea. After adding 200 ml of diethyl ether, 4-(4-chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrobromide was separated as an oil. The solvent was decanted, the product was dissolved in 30 ml of water and extracted with 100 ml of ethyl acetate. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, the amorphous residue was dissolved in 30 ml of ethanol and acidified with ethanolic hydrochloric acid. The solvent was distilled off, the residue was dissolved in 40 ml of water and the end product was obtained by lyophilization. Colorless amorphous solid body, decomposition beginning at 128° C, γ C=N1615 cm-1. was separated as an oil The solvent was decanted the product was dissolved in 30 ml of water extracted with 100 ml of ethyl acetate After drying over sodium sulfate the solvent was distilled off under reduced pressure the amorphous residue was dissolved in 30 ml of ethanol The solvent was distilled off the residue was dissolved in 40 ml of water the end product was obtained by lyophilization at 128° C

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

Procedure: 6.8 of 2-bromo-4'-chloro-3'-dimethylsulfamoylacetophenone were reacted according to Example 23 with 3.3 g of 1,3-dipropylthiourea. After adding 200 ml of diethyl ether, 4-(4-chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrobromide was separated as an oil. The solvent was decanted, the product was dissolved in 30 ml of water and extracted with 100 ml of ethyl acetate. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, the amorphous residue was dissolved in 30 ml of ethanol and acidified with ethanolic hydrochloric acid. The solvent was distilled off, the residue was dissolved in 40 ml of water and the end product was obtained by lyophilization. Colorless amorphous solid body, decomposition beginning at 128° C, γ C=N1615 cm-1. was separated as an oil The solvent was decanted the product was dissolved in 30 ml of water extracted with 100 ml of ethyl acetate After drying over sodium sulfate the solvent was distilled off under reduced pressure the amorphous residue was dissolved in 30 ml of ethanol The solvent was distilled off the residue was dissolved in 40 ml of water the end product was obtained by lyophilization at 128° C

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

Procedure: 5.3 g of 2,4'-dichloro-3'-sulfamoylacetophenone and 3.2 g of ground 1,3-dipropylthio urea were heated in 45 ml of methanol for 5 minutes to 50° C and stirred for another 30 minutes at room temperature. After pouring the reaction mixture into 120 ml of diethyl ether the end product was obtained as a visquous mass which crystallized under mild heating rapidly with ether. Colorless solid body: melting point: 175° C (decomposition). was obtained as a visquous mass which crystallized under mild heating rapidly with ether

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

Procedure: 5.3 g of 2,4'-dichloro-3'-sulfamoylacetophenone and 3.2 g of ground 1,3-dipropylthio urea were heated in 45 ml of methanol for 5 minutes to 50° C and stirred for another 30 minutes at room temperature. After pouring the reaction mixture into 120 ml of diethyl ether the end product was obtained as a visquous mass which crystallized under mild heating rapidly with ether. Colorless solid body: melting point: 175° C (decomposition). was obtained as a visquous mass which crystallized under mild heating rapidly with ether

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 6.8 g of 2-bromo-4'-chloro-3'-dimethylsulfamoylacetophenone were reacted according to Example 23 with 3.3 g of 1,3-dipropylthiourea. After adding 200 ml of diethyl ether, 4-(4-chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrobromide was separated as an oil. The solvent was decanted, the product was dissolved in 30 ml of water and extracted with 100 ml of ethyl acetate. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, the amorphous residue was dissolved in 30 ml of ethanol and acidified with ethanolic hydrochloric acid. The solvent was distilled off, the residue was dissolved in 40 ml of water and the end product was obtained by lyophilization. Colorless amorphous solid body, decomposition beginning at 128° C., γ C=N 1615 cm-1. was separated as an oil The solvent was decanted the product was dissolved in 30 ml of water extracted with 100 ml of ethyl acetate After drying over sodium sulfate the solvent was distilled off under reduced pressure the amorphous residue was dissolved in 30 ml of ethanol The solvent was distilled off the residue was dissolved in 40 ml of water the end product was obtained by lyophilization at 128° C.

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

Procedure: 5.3 g of 2,4'-dichloro-3'-sulfamoylacetophenone and 3.2 g of ground 1,3-dipropylthio urea were heated in 45 ml of methanol for 5 minutes to 50° C. and stirred for another 30 minutes at room temperature. After pouring the reaction mixture into 120 ml of diethyl ether the end product was obtained as a visquous mass which crystallized under mild heating rapidly with ether. Colorless solid body: melting point: 175° C. (decomposition). was obtained as a visquous mass which crystallized under mild heating rapidly with ether

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

Procedure: 2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (3.551 g., 0.015 mole) and 2.405 g. (0.015 mole) of 1,3-di-n-propylthiourea were dissolved in acetone and heated at reflux for 11/2 hours. The solution was concentrated to a volume of 50 ml. and cooled. A small amount of solid was removed by filtration. The filtrate was further concentrated to a volume of 25 ml. and ether was added to turbidity. After the reaction mixture had been cooled the yellow solid was collected by filtration to give 2.77 g. (46.6%) of the product, m.p. 129°-130° C. heated at reflux for 11/2 hours The solution was concentrated to a volume of 50 ml and cooled A small amount of solid was removed by filtration The filtrate was further concentrated to a volume of 25 ml and ether was added to turbidity After the reaction mixture had been cooled the yellow solid was collected by filtration to give 2.77 g

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

Procedure: 6.8 of 2-bromo-4'-chloro-3'-dimethylsulfamoylacetophenone were reacted according to Example 23 with 3.3 g of 1,3-dipropylthiourea. After adding 200 ml of diethyl ether, 4-(4-chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrobromide was separated as an oil. The solvent was decanted, the product was dissolved in 30 ml of water and extracted with 100 ml of ethyl acetate. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, the amorphous residue was dissolved in 30 ml of ethanol and acidified with ethanolic hydrochloric acid. The solvent was distilled off, the residue was dissolved in 40 ml of water and the end product was obtained by lyophilization. Colorless amorphous solid body, decomposition beginning at 128° C, γ C=N1615 cm-1. was separated as an oil The solvent was decanted the product was dissolved in 30 ml of water extracted with 100 ml of ethyl acetate After drying over sodium sulfate the solvent was distilled off under reduced pressure the amorphous residue was dissolved in 30 ml of ethanol The solvent was distilled off the residue was dissolved in 40 ml of water the end product was obtained by lyophilization at 128° C

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

Procedure: 5.3 g of 2,4'-dichloro-3'-sulfamoylacetophenone and 3.2 g of ground 1,3-dipropylthio urea were heated in 45 ml of methanol for 5 minutes to 50° C and stirred for another 30 minutes at room temperature. After pouring the reaction mixture into 120 ml of diethyl ether the end product was obtained as a visquous mass which crystallized under mild heating rapidly with ether. Colorless solid body: melting point: 175° C (decomposition). was obtained as a visquous mass which crystallized under mild heating rapidly with ether