2-benzoyl-3,3-bis(methylsulfanyl)prop-2-enenitrile

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

Procedure: A mixture of the 2-hydrazino-5-methylsulfonyl pyridine (180 mg, 0.81 mmol) and 1-benzoyl-2,2-bis(methylthio)-1-cyano ethene (201 mg, 0.81 mmol) in anhydrous ethanol was refluxed overnight. The resulting solution was cooled to room temperature, diluted with water (25 ml) and extracted with ethyl acetate (2×25 ml). The ethyl acetate layer was dried with sodium sulfate and concentrated to give crude product. Chromatography of the mixture led to the isolation of the desired product (26 mg, 9%) in the form of a white solid. was refluxed overnight extracted with ethyl acetate (2×25 ml) The ethyl acetate layer was dried with sodium sulfate concentrated to give crude product

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

Procedure: Following the method of Rudorf and Augustin (J. Prakt. Chem. 1978, 320, 576), a solution of 15.9 g (63.9 mmol) 2-benzoyl-3,3-bis(methylthio)acrylonitrile, 9.36 g (76.7 mmol) guanidine nitrate and 22.3 ml (160 mmol) triethylamine in 200 ml DMF was heated at reflux for 6 h. The reaction mixture was then cooled to room temperature. On addition of 300 ml water, a precipitate appeared which was collected by filtration and washed with water to afford 12.7 g (86%) 2-amino-4-(methylthio)-6-phenyl-pyrimidine-5-carbonitrile as a sand-coloured solid. EI-MS m-e (%): 242 (M+, 32), 241 ([M—H]+, 100). at reflux for 6 h was collected by filtration washed with water

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

Procedure: Following the method of Rudorf and Augustin (Phosphorus and Sulfur 1981, 9, 329), a solution of 15.0 g (103 mmol) benzoylacetonitrile in 200 ml dry DMSO was added dropwise to a stirred suspension of 8.27 g (206 mmol, 60% dispersion in mineral oil) sodium hydride in 200 ml DMSO under argon at room temperature. 6.23 ml (103 mmol) carbon disulfide was then added dropwise, with external water bath cooling, and stirring continued for 2 hours, after which 12.9 ml (206 mmol) methyl iodide was added dropwise, with external water bath cooling, and stirring continued for a further 16 h. The reaction mixture was then poured into 7.5 l ice-cold water, and the precipitate collected by filtration and dried in vacuo to afford 25.6 g (99%) 2-benzoyl-3,3-bis(methylthio)acrylonitrile none as a pale yellow crystalline solid. EI-MS m/e (%): 249 (M+, 8), 248 ([M—H]+, 17), 234 ([M—CH3]+, 25), 105 ([PhCO]+, 100), 77 ([Ph]+, 54). cooling cooling stirring continued for a further 16 h the precipitate collected by filtration dried in vacuo