2-[amino(methylsulfanyl)methylidene]propanedinitrile

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: Into a pressure bottle were placed 5.6 g of 3-amino-2-cyano-3-(methylthio)propenenitrile and 3 ml of dimethylformamide, and the mixture was cooled to 0°. A volume of 5.4 ml (3.6 g) of dimethylamine was condensed in a dry-ice trap and added to the pressure bottle. The bottle was sealed and the reaction mixture was heated, with stirring, at 100° for 3-4 hours (in subsequent runs, the heating time was reduced to 80 minutes without reducing the yield). After this time, the mixture was allowed to cool to ambient temperature, where it stood for two days. The pressure bottle was cooled to 0° and opened. The mixture was allowed to attain ambient temperature, then was poured into 300 ml of ice-water, causing a white solid to precipitate. The slurry was stirred for 30 minutes. The solid product was collected by filtration and washed with cold water to give 5.1 g of 3-amino-2-cyano-3-(dimethylamino)propenenitrile, m.p. 228°-229°. The nmr was consistent with the assigned structure. the mixture was cooled to 0° condensed in a dry-ice trap added to the pressure bottle The bottle was sealed the reaction mixture was heated the heating time was reduced to 80 minutes yield) where it stood for two days The pressure bottle was cooled to 0° to attain ambient temperature to precipitate The slurry was stirred for 30 minutes The solid product was collected by filtration washed with cold water

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

Procedure: Two liters of ethanol were saturated with ammonia gas at 15°. At ambient temperature, 278.3 g of 2-cyano-3,3-bis(methylthio)propenenitrile were added portionwise. A sodium hydroxide trap was used to trap the methyl mercaptan by-product. After complete addition of the propenenitrile the reaction mixture was cooled to approximately 10°. The solid which separated was collected by filtration and washed with cold ethanol to give, after drying, 206.3 g of white 3-amino-2-cyano-3-(methylthio)propenenitrile, m.p. 228°-230°. The nmr was consistent with the assigned structure. A sodium hydroxide trap was used to trap was cooled to approximately 10° The solid which separated was collected by filtration washed with cold ethanol to give after drying

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

Procedure: Two liters of ethanol were saturated with ammonia gas at 15°. At ambient temperature, 278.3 g of 2-cyano-3,3-bis(methylthio)propenenitrile were added portionwise. A sodium hydroxide trap was used to trap the methyl mercaptan by-product. After complete addition of the propenenitrile the reaction mixture was cooled to approximately 10°. The solid which separated was collected by filtration and washed with cold ethanol to give, after drying, 206.3 g of white 3-amino-2-cyano-3-(methylthio)propenenitrile, m.p. 228°-230°. The nmr was consistent with the assigned structure. A sodium hydroxide trap was used to trap was cooled to approximately 10° The solid which separated was collected by filtration washed with cold ethanol to give after drying

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

Procedure: At 15°, 650 ml of ethanol was saturated with gaseous ammonia. Seventy-three and three-tenths grams of 2-cyano-3,3-bis(methylthio)propenenitrile were added portionwise during 10 minutes. The reaction mixture was heated to 78° during 15 minutes. The slurry was allowed to cool to ambient temperature, then cooled to 10°. The solid was collected by filtration and washed with cold ethanol to give, when dried, m.p. 228°-229° (Literature m.p. 229°-230°, R. Gompper and W. Topel, Ber. 95, 2871 (1902)). At 15° The reaction mixture was heated to 78° during 15 minutes cooled to 10° The solid was collected by filtration washed with cold ethanol to give when dried

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

Procedure: Into a pressure bottle were placed 5.6 g of 3-amino-2-cyano-3-(methylthio)propenenitrile and 3 ml of dimethylformamide, and the mixture was cooled to 0°. A volume of 5.4 ml (3.6 g) of dimethylamine was condensed in a dry-ice trap and added to the pressure bottle. The bottle was sealed and the reaction mixture was heated, with stirring, at 100° for 3-4 hours (in subsequent runs, the heating time was reduced to 80 minutes without reducing the yield). After this time, the mixture was allowed to cool to ambient temperature, where it stood for two days. The pressure bottle was cooled to 0° and opened. The mixture was allowed to attain ambient temperature, then was poured into 300 ml of ice-water, causing a white solid to precipitate. The slurry was stirred for 30 minutes. The solid product was collected by filtration and washed with cold water to give 5.1 g of 3-amino-2-cyano-3-(dimethylamino)propenenitrile, m.p. 228°-229°. The nmr was consistent with the assigned structure. the mixture was cooled to 0° condensed in a dry-ice trap added to the pressure bottle The bottle was sealed the reaction mixture was heated the heating time was reduced to 80 minutes yield) where it stood for two days The pressure bottle was cooled to 0° to attain ambient temperature to precipitate The slurry was stirred for 30 minutes The solid product was collected by filtration washed with cold water

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

Procedure: Two liters of ethanol were saturated with ammonia gas at 15°. At ambient temperature, 278.3 g of 2-cyano-3,3-bis(methylthio)propenenitrile were added portionwise. A sodium hydroxide trap was used to trap the methyl mercaptan by-product. After complete addition of the propenenitrile the reaction mixture was cooled to approximately 10°. The solid which separated was collected by filtration and washed with cold ethanol to give, after drying, 206.3 g of white 3-amino-2-cyano-3-(methylthio)propenenitrile, m.p. 228°-230°. The nmr was consistent with the assigned structure. A sodium hydroxide trap was used to trap was cooled to approximately 10° The solid which separated was collected by filtration washed with cold ethanol to give after drying