1,3-dibutylthiourea

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

Procedure: 5.2 g of 2,4'-dichloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. the end product was precipitated with diisopropyl ether

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

Procedure: 5.2 g of 2,4'-dichloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. the end product was precipitated with diisopropyl ether

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

Procedure: 6.2 g of 2 bromo-4'-chloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. the end product was precipitated with diisopropyl ether

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

Procedure: was obtained in a manner analogous to the method described in Example 10 from 3.5 g of 2-bromo-2',4'-dichloro-5'-sulfamoylacetophenone and 1.9 g of 1.3-dibutyl-thiourea. M.p. 194° C (decomposition). was obtained in a manner analogous to the method

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

Procedure: was obtained in a manner analogous to the method described in Example 10 from 3.5 g of 2-bromo-2',4'-dichloro-5'-sulfamoylacetophenone and 1.9 g of 1.3-dibutyl-thiourea. M.p. 194° C (decomposition). was obtained in a manner analogous to the method

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 358 g of N,N'-dibutylthiourea and 225 g of malonic acid are dissolved in 850 ml of glacial acetic acid, with warming, 190 ml of acetic anhydride are added dropwise at 60° C., with stirring, the mixture is warmed at 70° C. for 2 hours, 100 ml of acetic anhydride are added dropwise, the resulting mixture is warmed at 70° C. for 1 hour, a further 100 ml of acetic anhydride are added dropwise, the resulting mixture is warmed at 90° C. for 3 hours and 70 ml of water are added dropwise at 60°-90° C. The solvent is distilled off in vacuo at 50°-90° C. and the residue is stirred with 1 l of methanol. The crystalline precipitate is filtered off, washed with methanol and dried in vacuo at 40° C. 212 g of N,N'-dibutyl-5-acetyl-thiobarbituric acid are obtained. with warming the resulting mixture is warmed at 70° C. for 1 hour the resulting mixture is warmed at 90° C. for 3 hours The solvent is distilled off in vacuo at 50°-90° C. the residue is stirred with 1 l of methanol The crystalline precipitate is filtered off washed with methanol dried in vacuo at 40° C

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

Procedure: 5.2 g of 2,4'-dichloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. Colorless crystalline solid body: melting point: 164° C. (decomposition). the end product was precipitated with diisopropyl ether

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

Procedure: 6.2 g of 2-bromo-4'-chloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. Colorless amorphous solid body: decomposition beginning at 100° C., γC=N 1615 cm-1. the end product was precipitated with diisopropyl ether beginning at 100° C.

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

Procedure: 2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (7.10 g., 0.03 mole) was dissolved in 125 ml. of acetone treated with Norit and filtered. The filtrate was added to 5.650 g. (0.03 mole) of 1,3-di-n-butylthiourea in 100 ml. of acetone. The solution was stirred at reflux under a nitrogen atmosphere for 6 hours, allowed to cool to room temperature, and stirred an additional 17 hours. The red solution was treated with Norit, filtered, and concentrated to a volume of 100 ml. The yellow solid that crystallized out was collected by filtration, washed and dried to give the 6.05 g. (47.5% yield) of product, m.p. 138°-139° C. (dec.). filtered The filtrate was added to 5.650 g at reflux under a nitrogen atmosphere for 6 hours stirred an additional 17 hours filtered concentrated to a volume of 100 ml The yellow solid that crystallized out was collected by filtration washed dried to give the 6.05 g

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

Procedure: 2-Chloro-3-methylquinoxaline (3.572 g., 0.02 mole) was dissolved in 50 ml. of methanol, treated with Norit and filtered. The filtrate was added to 3.767 g. (0.02 mole) of 1,3-dibutylthiourea dissolved in 25 ml. of methanol. The resulting solution was stirred at room temperature for 1 hour and evaporated on a rotary evaporator. The residual oil was triturated successively with several portions of ether, 2:1 pentane-ether and acetone, and was filtered and washed with pentane, to give 2.60 g. (38.6%) of product as a tan solid, m.p. 97°-99°. filtered The filtrate was added to 3.767 g evaporated on a rotary evaporator The residual oil was triturated successively with several portions of ether, 2:1 pentane-ether and acetone was filtered washed with pentane to give 2.60 g

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

Procedure: 5.2 g of 2,4'-dichloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. the end product was precipitated with diisopropyl ether

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

Procedure: 6.2 g of 2 bromo-4'-chloro-3'-sulfamoylacetophenone were reacted with 3.8 g of 1,3-di-n-butylthiourea according to the prescription given in Example 12 and the end product was precipitated with diisopropyl ether. the end product was precipitated with diisopropyl ether