2-[anilino(methylsulfanyl)methylidene]propanedinitrile

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

Procedure: A mixture of compound 6 (3.2258 g, 14.85 mmol) and hydrazine (742 mg, 23.16 mmol) in EtOH (20 mL) was refluxed for 30 min, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried to give compound 7 (2.599 g, 88.1% yield, 99.8% purity) as a white powder. was refluxed for 30 min, at which time the reaction The resulting precipitate was filtered dried

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

Procedure: A mixture of compound 6 (3.2258 g, 14.85 mmol) and hydrazine (742 mg, 23.16 mmol) in EtOH (20 mL) was refluxed for 30 min, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried to give compound 7 (2.599 g, 88.1% yield, 99.8% purity) as a white powder. was refluxed for 30 min, at which time the reaction The resulting precipitate was filtered dried

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

Procedure: To a solution of malononitrile (1.0 g, 15.14 mmol) in DMF 20 mL was added TEA (2.099 mL, 15.14 mmol). After the mixture was stirred at room temperature for 5 min, phenylisothiocynate (2.047 g, 15.14 mmol) was added dropwise to the mixture. The reaction mixture was stirred at room temperature for 30 min. After the reaction was complete as determined by TLC, methyl iodide (2.149 g, 15.14 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried in an oven overnight to give compound 6 (3.226 g, 98.2% yield, 97.4% purity) as a light yellow solid. The reaction mixture was stirred at room temperature for 30 min was added the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction The resulting precipitate was filtered dried in an oven overnight

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

Procedure: A mixture of compound 6 (3.2258 g, 14.85 mmol) and hydrazine (742 mg, 23.16 mmol) in EtOH (20 mL) was refluxed for 30 min, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried to give compound 7 (2.599 g, 88.1% yield, 99.8% purity) as a white powder. was refluxed for 30 min, at which time the reaction The resulting precipitate was filtered dried

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

Procedure: A mixture of compound 6 (3.2258 g, 14.85 mmol) and hydrazine (742 mg, 23.16 mmol) in EtOH (20 mL) was refluxed for 30 min, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried to give compound 7 (2.599 g, 88.1% yield, 99.8% purity) as a white powder. was refluxed for 30 min, at which time the reaction The resulting precipitate was filtered dried

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

Procedure: To a solution of malononitrile (1.0 g, 15.14 mmol) in DMF 20 mL was added TEA (2.099 mL, 15.14 mmol). After the mixture was stirred at room temperature for 5 min, phenylisothiocynate (2.047 g, 15.14 mmol) was added dropwise to the mixture. The reaction mixture was stirred at room temperature for 30 min. After the reaction was complete as determined by TLC, methyl iodide (2.149 g, 15.14 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried in an oven overnight to give compound 6 (3.226 g, 98.2% yield, 97.4% purity) as a light yellow solid. The reaction mixture was stirred at room temperature for 30 min was added the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction The resulting precipitate was filtered dried in an oven overnight

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

Procedure: Dissolved 2-((methylthio)(phenylamino)methylene)malononitrile (3.2 g) in EtOH (100 mL) and added hydrazine hydrate (1 eq), then heated to reflux until complete by TLC (absence of starting material, 18 hrs). Poured into ice water and filtered to obtain 5-amino-3-(phenylamino)-1H-pyrazole-4-carbonitrile as a yellow powder. heated to reflux until complete by TLC (absence of starting material, 18 hrs) filtered

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

Procedure: Dissolved malononitrile (5.0 g) in DMF (50 mL), added triethylamine (1 eq., 10.49 mL), and stirred for 5 minutes before adding phenylisothiocyanate (1 eq) dropwise, then stirred until complete by TLC (absence of phenylisothiocyanate, 3 hrs). Added methyl iodide (1 eq) dropwise, then stirred until intermediate was fully consumed (absent on TLC, 18 hrs); poured into 100 mL ice water, then filtered resulting solution to obtain 2-((methylthio)(phenylamino)methylene)malononitrile as a white powder. was fully consumed (absent on TLC, 18 hrs) poured into 100 mL ice water filtered resulting solution

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

Procedure: A mixture of compound 6 (3.2258 g, 14.85 mmol) and hydrazine (742 mg, 23.16 mmol) in EtOH (20 mL) was refluxed for 30 min. at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried to give compound 7 (2.599 g, 88.1% yield, 99.8% purity) as a white powder. was refluxed for 30 min. at which time the reaction The resulting precipitate was filtered dried

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

Procedure: A mixture of compound 6 (3.2258 g, 14.85 mmol) and hydrazine (742 mg, 23.16 mmol) in EtOH (20 mL) was refluxed for 30 min. at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried to give compound 7 (2.599 g, 88.1% yield, 99.8% purity) as a white powder. was refluxed for 30 min. at which time the reaction The resulting precipitate was filtered dried

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

Procedure: To a solution of malononitrile (1.0 g, 15.14 mmol) in DMF 20 mL was added triethylamine (2.099 mL, 15.14 mmol). After the mixture was stirred at room temperature for 5 min, phenylisothiocyanate (2.047 g, 15.14 mmol) was added dropwise to the mixture. The reaction mixture was stirred at room temperature for 30 min. After the reaction was complete as determined by TLC, methyl iodide (2.149 g, 15.14 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried in an oven overnight to give compound 6 (3.226 g, 98.2% yield, 97.4 purity) as a light yellow solid. The reaction mixture was stirred at room temperature for 30 min was added the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction The resulting precipitate was filtered dried in an oven overnight

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

Procedure: To a solution of malononitrile (1.0 g, 15.14 mmol) in DMF 20 mL was added triethylamine (2.099 mL, 15.14 mmol). After the mixture was stirred at room temperature for 5 min, phenylisothiocyanate (2.047 g, 15.14 mmol) was added dropwise to the mixture. The reaction mixture was stirred at room temperature for 30 min. After the reaction was complete as determined by TLC, methyl iodide (2.149 g, 15.14 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried in an oven overnight to give compound 6 (3.226 g, 98.2% yield, 97.4 purity) as a light yellow solid. The reaction mixture was stirred at room temperature for 30 min was added the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction The resulting precipitate was filtered dried in an oven overnight