2,2-dimethylpropanoyl cyanide

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

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

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

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

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

Procedure: 200 ml of concentrated sulphuric acid and then 72 g of water were added dropwise to 111 g (1 mol) of pivaloyl cyanide at 20° to 25° C. The reaction mixture was subsequently stirred at 20° to 25° C. for 20 hours and was added to a solution of 106 g (1 mol) of thiocarbohydrazide in 500 ml of water and 150 ml of concentrated hydrochloric acid at the above temperature. The mixture was subsequently stirred at 80° to 90° C. for 2 hours, cooled to 5° to 10° C. and filtered. The solid residue was recrystallized from methanol. 130 g (65% of theory) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (VII) of melting point 216° C. were obtained. The mixture was subsequently stirred at 80° to 90° C. for 2 hours cooled to 5° to 10° C. filtered The solid residue was recrystallized from methanol

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

Procedure: 200 ml of concentrated sulphuric acid and then 72 g of water were added dropwise to 111 g (1 mol) of pivaloyl cyanide at 20° to 25° C. The reaction mixture was subsequently stirred at 20° to 25° C. for 20 hours and was added to a solution of 106 g (1 mol) of thiocarbohydrazide in 500 ml of water and 150 ml of concentrated hydrochloric acid at the above temperature. The mixture was subsequently stirred at 80° to 90° C. for 2 hours, cooled to 5° to 10° C. and filtered. The solid residue was recrystallized from methanol. 130 g (65% of theory) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (VII) of melting point 216° C. were obtained. The mixture was subsequently stirred at 80° to 90° C. for 2 hours cooled to 5° to 10° C. filtered The solid residue was recrystallized from methanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydrogen chloride gas was passed into a mixture of 222 g (2 mol) of pivaloyl cyanide and 120 g (2 mol) of glacial acetic acid under 8 bars and at 20° to 25° C. for four hours. Thereafter, the mixture was let down and excess glacial acetic acid was stripped off in vacuo. The product was then added to a mixture of 212 g (2 mol) of thiocarbohydrazide, 840 g of water and 280 g of concentrated hydrochloric acid. When the addition had ended, the reaction mixture was warmed to 90° C. for 1.5 hours and then subsequently stirred at room temperature overnight. The mixture was then cooled to 0° C. and the solid obtained was filtered off, washed with 400 ml of cold water and dried at 40° C. in vacuo. 314.4 g (78.6% of theory) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (VII) of melting point 205°-209° C. were obtained. When the addition The mixture was then cooled to 0° C. the solid obtained was filtered off washed with 400 ml of cold water dried at 40° C. in vacuo

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

Procedure: 55.5 g (0.5 mole) of pivaloyl cyanide and 2 g of ammonium chloride were introduced into a 500 ml three-necked flask. The mixture was cooled to -5° to 0° C. and 100 ml of concentrated sulphuric acid was added dropwise at this temperature. 18 ml (1 mole) of water were then added dropwise, also at -5° to 0° C. The reaction mixture was subsequently stirred at -5° to 0° C. for 12 hours and was then poured onto a solution of 350 g of sodium carbonate in 600 ml of water. It was extracted twice with 300 ml of methylene chloride each time. The combined organic phases were washed with 300 ml of water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. Recrystallization from petroleum ether gave 66 g (51.2% of theory) of trimethylpyruvic acid amide of melting point 67° to 69° C. The mixture was cooled to -5° to 0° C. It was extracted twice with 300 ml of methylene chloride each time The combined organic phases were washed with 300 ml of water dried over sodium sulphate concentrated by distilling off the solvent in vacuo Recrystallization from petroleum ether

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

Procedure: Hydrogen chloride was passed into a mixture of 60 g (1 mole) of glacial acetic acid and 111.0 g (1 mole) of pivaloyl cyanide at 20° to 25° C. and under 8 bars for 5 hours. The reaction mixture was then let down and poured onto an excess of a saturated sodium bicarbonate solution. The mixture was extracted three times with 200 ml of methylene chloride each time. The combined organic phases were washed with 200 ml of water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The residue which remained crystallized after a short time. Recrystallization from petroleum ether gave 97 g (75.2% of theory) of trimethylpyruvic acid amide of melting point 68° to 69° C. The mixture was extracted three times with 200 ml of methylene chloride each time The combined organic phases were washed with 200 ml of water dried over sodium sulphate concentrated by distilling off the solvent in vacuo The residue which remained crystallized after a short time Recrystallization from petroleum ether

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

Procedure: Hydrogen chloride was passed into a mixture of 60 g (1 mole) of glacial acetic acid and 111.0 g (1 mole) of pivaloyl cyanide at 20° to 25° C. and under 8 bars for 5 hours. The reaction mixture was then let down and poured onto an excess of a saturated sodium bicarbonate solution. The mixture was extracted three times with 200 ml of methylene chloride each time. The combined organic phases were washed with 200 ml of water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The residue which remained crystallized after a short time. Recrystallization from petroleum ether gave 97 g (75.2% of theory) of trimethylpyruvic acid amide of melting point 68° to 69° C. The mixture was extracted three times with 200 ml of methylene chloride each time The combined organic phases were washed with 200 ml of water dried over sodium sulphate concentrated by distilling off the solvent in vacuo The residue which remained crystallized after a short time Recrystallization from petroleum ether

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

Procedure: 111.0 g (1 mole) of pivaloyl cyanide were added dropwise to 800 g of a 36% strength solution of hydrogen bromide in glacial acetic acid at room temperature, while stirring. When the addition had ended, the mixture was subsequently stirred at room temperature for 3 hours. 9 ml (0.5 mole) of water were then added dropwise at 20° to 25° C. and the mixture was subsequently stirred at room temperature for 1 hour. The reaction solution was then poured into an excess of saturated sodium bicarbonate solution. It was extracted three times with 200 ml of methylene chloride each time. The combined organic phases were washed with 200 ml of water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. After some time, the oil which remained crystallized completely. The recrystallization from petroleum ether gave 113.5 g (88% of theory) of trimethylpyruvic acid amide of melting point 69° to 70° C. When the addition the mixture was subsequently stirred at room temperature for 3 hours the mixture was subsequently stirred at room temperature for 1 hour It was extracted three times with 200 ml of methylene chloride each time The combined organic phases were washed with 200 ml of water dried over sodium sulphate concentrated by distilling off the solvent in vacuo After some time, the oil which remained crystallized completely The recrystallization from petroleum ether

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

Procedure: First 5.12 kg (50 mols) of acetic anhydride and then 2.78 kg (25 mols) of pivaloyl cyanide were introduced, in each case at room temperature, into 9.81 kg (100 mols) of concentrated sulphuric acid which had been initially introduced into the reaction vessel. After subsequently stirring this reaction mixture for 2 hours, it was stirred into a solution of 2.66 kg (25 mols) of thiocarbohydrazide in 30 liters of 1 N HCl at 20°-30° C. When the addition had ended, the mixture was subsequently stirred for a further 2 hours at 50°-55° C.; after cooling, the reaction product which had precipitated was filtered off, washed with 20 liters of water and dried. 4.80 kg (96% of theory) of 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one (V) were obtained as colorless crystals of melting point 212°-214° C.; content, according to determination by gas chromatography, >99%. had been initially introduced into the reaction vessel When the addition the mixture was subsequently stirred for a further 2 hours at 50°-55° C. after cooling the reaction product which had precipitated was filtered off washed with 20 liters of water dried