2-isothiocyanato-2-methylbutane

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

Procedure: To a suspension of monosodium cyanamide (0.64 g, 10 mmol) in absolute ethanol (30 mL), 1,1-dimethylpropylisothiocyanate (1.29 g, 10 mmol) was added slowly at room temperature. Exothermic reaction occurred during addition and near the end of the addition, the initially heterogeneous mixture became a homogeneous solution. It was allowed to stir at room temperature for 2 hours and then heated at 75° C. for 1 hour. The reaction mixture was cooled to room temperature and the solid was filtered. The filtrate solution was concentrated to yield the title A compound (1.6 g) as a colorless solid. was added slowly at room temperature Exothermic reaction occurred during addition and near the end of the addition heated at 75° C. for 1 hour The reaction mixture was cooled to room temperature the solid was filtered The filtrate solution was concentrated

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

Procedure: To a suspension of monosodium cyanamide (0.64 g, 10 mmol) in absolute ethanol (30 mL), 1,1-dimethylpropylisothiocyanate (1.29 g, 10 mmol) was added slowly at room temperature. Exothermic reaction occurred during addition and near the end of the addition, the initially heterogeneous mixture became a homogeneous solution. It was allowed to stir at room temperature for 2 hours and then heated at 75° C. for 1 hour. The reaction mixture was cooled to room temperature and the solid was filtered. The filtrate solution was concentrated to yield the title A compound (1.6 g) as a colorless solid. was added slowly at room temperature Exothermic reaction occurred during addition and near the end of the addition heated at 75° C. for 1 hour The reaction mixture was cooled to room temperature the solid was filtered The filtrate solution was concentrated

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

Procedure: To a solution of 3-ethyl-4-aminobenzonitrile (1.35 g, 9.29 mmol) in DMF (10 mL) at room temperature was added sodium hydride (0.28 g, 80%, 9.29 mmol). The mixture was heated to 70° C. for 40 minutes and was then cooled to room temperature. A solution of tert-amyl isothiocyanate (1.0 g, 7.74 mmol) in DMF (1 mL) was added by syringe and the reaction was stirred at 70° C. overnight. The cooled reaction mixture was diluted with 2N HCl and water and the mixture was extracted with ethyl acetate. The organic phase was dried and concentrated to afford an oil. The crude product was taken up in a minimal amount of diethyl ether and the solution was made turbid by adding petroleum ether. Sonication resulted in the formation of a precipitate which was collected by filtration to afford 1.2 g (56%) of 1-(2-ethyl-4-cyanophenyl)-3-(1,1-dimethyl-propyl)-thiourea as an off-white solid which was used without further purification. was then cooled to room temperature The cooled reaction mixture the mixture was extracted with ethyl acetate The organic phase was dried concentrated to afford an oil Sonication resulted in the formation of a precipitate which was collected by filtration

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

Procedure: To a suspension of monosodium cyanamide (0.64 g, 10 mmol) in absolute ethanol (30 mL), 1,1-dimethylpropylisothiocyanate (1.29 g, 10 mmol) was added slowly at room temperature. Exothermic reaction occurred during addition and near the end of the addition, the initially heterogeneous mixture became a homogeneous solution. It was allowed to stir at room temperature for 2 hours and then heated at 75° C. for 1 hour. The reaction mixture was cooled to room temperature and the solid was filtered. The filtrate solution was concentrated to yield the title A compound (1.6 g) as a colorless solid. was added slowly at room temperature Exothermic reaction occurred during addition and near the end of the addition heated at 75° C. for 1 hour The reaction mixture was cooled to room temperature the solid was filtered The filtrate solution was concentrated