ethyl butanimidate;hydrochloride

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

Procedure: 2.90 g (14.48 mol) of 2-guanidino-4-thiazole carboxylic acid hydrazide in 50 ml dry ethanol was slurried with 29.1 mmol of ethyl butyrimidate (prepared from 4.41 g (29.1 mmol) of ethylbutyrimidate hydrochloride) for 5 days at 25°. The slurry was filtered and washed with ethanol and ether and dried to give 3.071 g (78%) of 2-guanidino-4-thiazole carboxylic acid 2-butyriminohydrazide. The slurry was filtered washed with ethanol and ether dried

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

Procedure: 2.90 g (14.48 mol) of 2-guanidino-4-thiazole carboxylic acid hydrazide in 50 ml dry ethanol was slurried with 29.1 mmol of ethyl butyrimidate (prepared from 4.41 g (29.1 mmol) of ethylbutyrimidate hydrochloride) for 5 days at 25°. The slurry was filtered and washed with ethanol and ether and dried to give 3.071 g (78%) of 2-guanidino-4-thiazole carboxylic acid 2-butyriminohydrazide. The slurry was filtered washed with ethanol and ether dried

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

Procedure: A solution of butyronitrile (15 g, 0.21 mol) in EtOH (150 mL) was cooled in an ice bath. The cold solution was then saturated with hydrogen chloride. The reaction mixture was refrigerated for 18 hours. The ethanol was evaporated under vacuum. The residual oily substance was then treated with ether to obtain the title compound (15.5 g, 48% yield) which was used in the next reaction. The ethanol was evaporated under vacuum The residual oily substance was then treated with ether

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

Procedure: 2.90 g (14.48 mol) of 2-guanidino-4-thiazole carboxylic acid hydrazide in 50 ml dry ethanol was slurried with 29.1 mmol of ethyl butyrimidate (prepared from 4.41 g (29.1 mmol) of ethylbutyrimidate hydrochloride) for 5 days at 25°. The slurry was filtered and washed with ethanol and ether and dried to give 3.071 g (78%) of 2-guanidino-4-thiazole carboxylic acid 2-butyriminohydrazide. The slurry was filtered washed with ethanol and ether dried

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

Procedure: A mixture of ethyl-butyroimidate hydrochloride (7.6 g, 50 mmol) and 4-nitro-1,2-phenylenediamine (7.6 g, 50 mmol) in ethanol (100 mL) was refluxed for 18 hours. The ethanol was evaporated under vacuum. The sticky solid was suspended in H2O (100 mL). Separation of the yellow solid gave the title compound (5.3 g, 52% yield). 1H-NMR (DMSO-d6 ; 200 MHz) δ 12.9 (s, 1H), 8.4 (s, 1H), 8.0-8.05 (d, 1H), 7.6-7.64 (d, 1H), 2.8-2.85 (t, 2H), 1.7-1.85 (m, 2H), 0.9-1.0 ppm (t, 3H), was refluxed for 18 hours The ethanol was evaporated under vacuum Separation of the yellow solid

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

Procedure: A mixture of ethyl-butyroimidate hydrochloride (7.6 g, 50 mmol) and 4-nitro-1,2-phenylenediamine (7.6 g, 50 mmol) in ethanol (100 mL) was refluxed for 18 hours. The ethanol was evaporated under vacuum. The sticky solid was suspended in H2O (100 mL). Separation of the yellow solid gave the title compound (5.3 g, 52% yield). 1H-NMR (DMSO-d6 ; 200 MHz) δ 12.9 (s, 1H), 8.4 (s, 1H), 8.0-8.05 (d, 1H), 7.6-7.64 (d, 1H), 2.8-2.85 (t, 2H), 1.7-1.85 (m, 2H), 0.9-1.0 ppm (t, 3H), was refluxed for 18 hours The ethanol was evaporated under vacuum Separation of the yellow solid

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

Procedure: A mixture of ethyl-butyroimidate hydrochloride (7.6 g, 50 mmol) and 4-nitro-1,2-phenylenediamine (7.6 g, 50 mmol) in ethanol (100 mL) was refluxed for 18 hours. The ethanol was evaporated under vacuum. The sticky solid was suspended in H2O (100 mL). Separation of the yellow solid gave the title compound (5.3 g, 52% yield). 1H-NMR (DMSO-d6 ; 200 MHz) δ 12.9 (s, 1H), 8.4 (s, 1H), 8.0-8.05 (d, 1H), 7.6-7.64 (d, 1H), 2.8-2.85 (t, 2H), 1.7-1.85 (m, 2H), 0.9-1.0 ppm (t, 3H), was refluxed for 18 hours The ethanol was evaporated under vacuum Separation of the yellow solid

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

Procedure: A solution of butyronitrile (15 g, 0.21 mol) in EtOH (150 mL) was cooled in an ice bath. The cold solution was then saturated with hydrogen chloride. The reaction mixture was refrigerated for 18 hours. The ethanol was evaporated under vacuum. The residual oily substance was then treated with ether to obtain the title compound (15.5 g, 48% yield) which was used in the next reaction. The ethanol was evaporated under vacuum The residual oily substance was then treated with ether

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

Procedure: A solution of butyronitrile (15 g, 0.21 mol) in EtOH (150 mL) was cooled in an ice bath. The cold solution was then saturated with hydrogen chloride. The reaction mixture was refrigerated for 18 hours. The ethanol was evaporated under vacuum. The residual oily substance was then treated with ether to obtain the title compound (15.5 g, 48% yield) which was used in the next reaction. The ethanol was evaporated under vacuum The residual oily substance was then treated with ether

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

Procedure: 2.90 g (14.48 mol) of 2-guanidino-4-thiazole carboxylic acid hydrazide in 50 ml dry ethanol was slurried with 29.1 mmol of ethyl butyrimidate (prepared from 4.41 g (29.1 mmol) of ethylbutyrimidate hydrochloride) for 5 days at 25°. The slurry was filtered and washed with ethanol and ether and dried to give 3.071 g (78%) of 2-guanidino-4-thiazole carboxylic acid 2-butyriminohydrazide. The slurry was filtered washed with ethanol and ether dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl butyrimidate hydrochloride from Example B (71.5 g, 472 mmol) is introduced into triethylamine (65 ml, 472 mmol) and cooled to 0° C. 2-Ethoxybenzohydrazide from Example A (85 g, 472 mmol) is suspended in 250 ml of isopropanol and added to the ethyl butyrimidate mixture. The reaction mixture is stirred at room temperature for 48 hours, the solid (triethylamine hydrochloride) is removed, and 25% strength hydrochloric acid (150 ml, 1.18 mol) is slowly added dropwise to the mother liquor at 0° C. to 5° C. The suspension of crystals is then stirred at 0° C. to 5° C. for 1 hour and the crystals are filtered with suction through a sintered funnel, washed with 100 ml of cold isopropanol and dried in a vacuum oven at 30° C. and 300 mbar overnight. the solid (triethylamine hydrochloride) is removed The suspension of crystals is then stirred at 0° C. to 5° C. for 1 hour the crystals are filtered with suction through a sintered funnel washed with 100 ml of cold isopropanol dried in a vacuum oven at 30° C. 300 mbar overnight

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Butyronitrile (85 ml, 839 mmol) is dissolved in absolute ethanol (65 ml, 961 mmol) and cooled to 0° C. to 5° C. While cooling further, gaseous hydrogen chloride (about 40 g, about 1.1 mol, differential weighing of the pressure cylinder) is passed into the solution. The reaction mixture is left at about 4° C. for 96 hours and then, while stirring, 260 ml of diisopropyl ether are added, and the mixture is cooled to −20° C. and filtered with suction at 0° C. through a sintered funnel. The crystals are rapidly (the product is hygroscopic) washed twice with 50 ml of cold diisopropyl ether each time and stored, sealed air-tight, in a refrigerator. cooled to 0° C. to 5° C While cooling further filtered with suction at 0° C. through a sintered funnel washed twice with 50 ml of cold diisopropyl ether each time sealed air-tight, in a refrigerator