2-amino-4-tert-butylfuran-3-carbonitrile

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

Procedure: To 4.0 g of 2-amino-3-cyano-4-(1,1-dimethylethyl)furan and 4.3 g of 2-methyl-4-chlorobutyryl chloride was added 150 ml of toluene. The reaction mixture was allowed to reflux for about 72 hours. The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 1.3 g of N-[3-cyano-4-(1,1-dimethylethyl)-2-furyl]-3-methyl-2-pyrrolidinone. mp=88°-90° C. Yield 21%. to reflux for about 72 hours The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water The organic phase was dried over anhydrous magnesium sulfate filtered concentrated under vacuum The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate Fractions containing the major component the solvent was evaporated

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

Procedure: To 4.0 g of 2-amino-3-cyano-4-(1,1-dimethylethyl)furan and 4.3 g of 2-methyl-4-chlorobutyryl chloride was added 150 ml of toluene. The reaction mixture was allowed to reflux for about 72 hours. The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 1.3 g of N-[3-cyano-4-(1,1-dimethylethyl)-2-furyl]-3-methyl-2-pyrrolidinone. mp=88°-90° C. Yield 21%. to reflux for about 72 hours The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water The organic phase was dried over anhydrous magnesium sulfate filtered concentrated under vacuum The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate Fractions containing the major component the solvent was evaporated

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

Procedure: 26.2 g (0.2 mole) of ethoxyacetyl chloride were added dropwise to a solution of 32.8 g (0.2 mole) of 2-amino-3-cyano-4-tert.-butyl-furan in 200 ml of dimethylformamide at room temperature. After the moderately exothermic reaction had subsided (rise in temperature from 23° C. to 38°), the reaction mixture was poured into ice-water. The solid product thereby obtained was filtered off and recrystallized, in the moist state, from a little methanol. 39.3 g of 2-ethoxyacetylamino-3-cyano-4-tert.-butyl-furan of melting point 98° C. were obtained in this manner. After the moderately exothermic reaction (rise in temperature from 23° C. to 38°) The solid product thereby obtained was filtered off recrystallized, in the moist state, from a little methanol

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

Procedure: 16.4 g (0.1 mole) of 2-amino-3-cyano-4-tert.-butylfuran were heated to 100° C. with 24 ml (0.4 mole) of acetic acid and 10.4 ml (0.11 mole) of acetic anhydride for one hour. Thereafter, the reaction mixture was evaporated under reduced pressure and the residue was recrystallized from a mixture of toluene/cyclohexane (1:2). 17.2 g of 2-acetylamino-3-cyano-4-tert.-butyl-furan of melting point 135° C. were obtained in this manner. Thereafter, the reaction mixture was evaporated under reduced pressure the residue was recrystallized from a mixture of toluene/cyclohexane (1:2)

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

Procedure: 174 g (2 moles) of morpholine were added dropwise to a solution of 232 g (2 moles) of hydroxy-pinacolone and 132 g (2 moles) of malonic acid dinitrile in 500 ml of dimethylformamide, while cooling, in a manner such that the internal temperature did not rise above 40° C. After the reaction had ended, the reaction mixture was stirred into 5 liters of ice-water. The solid product which thereby precipitated was filtered off, washed with water and dried. 170 g of 2-amino-3-cyano-4-tert.-butyl-furan of melting point 86° C. were obtained in this manner. while cooling, in a manner such that the internal temperature did not rise above 40° C The solid product which thereby precipitated was filtered off washed with water dried

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

Procedure: To 4.0 g of 2-amino-3-cyano-4-(1,1-dimethylethyl)furan and 4.3 g of 2-methyl-4-chlorobutyryl chloride was added 150 ml of toluene. The reaction mixture was allowed to reflux for about 72 hours. The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 1.3 g of N-[3-cyano-4-(1,1-dimethylethyl)-2-furyl]-3-methyl-2-pyrrolidinone. mp=88°-90° C. Yield 21%. to reflux for about 72 hours The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water The organic phase was dried over anhydrous magnesium sulfate filtered concentrated under vacuum The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate Fractions containing the major component the solvent was evaporated