phenylcyanamide

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: A mixture of 2-Amino-1-(4-aminophenyl)benzimidazole Hydrochloride (1.58 g, 6.06 mmol), phenylcyanamide (2.79 g, 23.6 mmol) and acetonitrile (10 ml) was refluxed for 3 days. The solid product was filtered off. The product was recrystallized from acetonitrile (300 ml). Yield 1.3 g, 57%. M.p. 265-267° C. was refluxed for 3 days The solid product was filtered off The product was recrystallized from acetonitrile (300 ml)

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

Procedure: N-phenylcyanamide was dissolved in EtOH (7 mL) and treated with H2NOH (1.5 eq of a 50% aq solution). The mixture was stirred at room temperature for 12 hours then reduced to dryness to afford 2-hydroxy-1-phenylguanidine (5) as a clear yellow oil, which was used without purification.

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

Procedure: To a solution of BrCN (0.11 g, 1.1 mmol) in MeOH (10 mL) at 0° C. was added solid KOAc (0.32 g, 3.3 mmol) and a solution of aniline (0.1 mL, 1.1 mmol) in MeOH (1 mL). The reaction was stirred for 3 hours then partitioned with water (15 mL) and dichloromethane (25 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness to afford N-phenylcyanamide, which was immediately used without purification. then partitioned with water (15 mL) and dichloromethane (25 mL) The organic layer was separated washed with brine dried over magnesium sulfate filtered

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

Procedure: In a flask were combined 3.0 grams (g) (25.4 mmol) phenyl cyanamide, 1.83 g (25.4 mmol) 1,2-epoxy butane, 3.51 g (25.4 mmol) potassium carbonate and 50 milliliters (ml) methyl ethyl ketone. The mixture was stirred overnight under a nitrogen blanket at room temperature. It was then filtered and the methyl ethyl ketone removed in vacuo. The solids recovered from the filter were extracted with acetone and combined with the residue from the main portion. The combined solids were dissolved in water and extraced with 15% isopropanol in chloroform. The solvents were removed in vacuo producing 2.30 g (48% of theoretical yield) of the desired product. Spectroscopic analysis confirmed the structure of the desired product. No type II product was detected. In a flask were combined It was then filtered the methyl ethyl ketone removed in vacuo The solids recovered from the filter were extracted with acetone The combined solids were dissolved in water The solvents were removed in vacuo producing

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

Procedure: In a flask were combined 3.0 grams (g) (25.4 mmol) phenyl cyanamide, 1.83 g (25.4 mmol) 1,2-epoxy butane, 3.51 g (25.4 mmol) potassium carbonate and 50 milliliters (ml) methyl ethyl ketone. The mixture was stirred overnight under a nitrogen blanket at room temperature. It was then filtered and the methyl ethyl ketone removed in vacuo. The solids recovered from the filter were extracted with acetone and combined with the residue from the main portion. The combined solids were dissolved in water and extraced with 15% isopropanol in chloroform. The solvents were removed in vacuo producing 2.30 g (48% of theoretical yield) of the desired product. Spectroscopic analysis confirmed the structure of the desired product. No type II product was detected. In a flask were combined It was then filtered the methyl ethyl ketone removed in vacuo The solids recovered from the filter were extracted with acetone The combined solids were dissolved in water The solvents were removed in vacuo producing

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

Procedure: N-phenylcyanamide was dissolved in EtOH (7 mL) and treated with H2NOH (1.5 eq of a 50% aq solution). The mixture was stirred at room temperature for 12 hours then reduced to dryness to afford 2-hydroxy-1-phenylguanidine (5) as a clear yellow oil, which was used without purification.

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

Procedure: To a solution of BrCN (0.11 g, 1.1 mmo) in MeOH (10 mL) at 0° C. was added solid KOAc (0.32 g, 3.3 mmol) and a solution of aniline (0.1 mL, 1.1 mmol) in MeOH (1 mL). The reaction was stirred for 3 hours then partitioned with water (15 mL) and dichloromethane (25 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness to afford N-phenylcyanamide, which was immediately used without purification. then partitioned with water (15 mL) and dichloromethane (25 mL) The organic layer was separated washed with brine dried over magnesium sulfate filtered

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

Procedure: To a solution of BrCN (0.11 g, 1.1 mmo) in MeOH (10 mL) at 0° C. was added solid KOAc (0.32 g, 3.3 mmol) and a solution of aniline (0.1 mL, 1.1 mmol) in MeOH (1 mL). The reaction was stirred for 3 hours then partitioned with water (15 mL) and dichloromethane (25 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness to afford N-phenylcyanamide, which was immediately used without purification. then partitioned with water (15 mL) and dichloromethane (25 mL) The organic layer was separated washed with brine dried over magnesium sulfate filtered

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

Procedure: A mixture of 2-Amino-1-(4-aminophenyl)benzimidazole hydrochloride (1.58 g, 6.06 mmol), phenylcyanamide (2.79 g, 23.6 mmol) and acetonitrile (10 ml) was refluxed for 3 days. The solid product was filtered off. The product was recrystallized from acetonitrile (300 ml). Yield 1.3 g, 57%. M.p. 265-267° C. was refluxed for 3 days The solid product was filtered off The product was recrystallized from acetonitrile (300 ml)

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

Procedure: A mixture of 2-Amino-1-(4-aminophenyl)benzimidazole hydrochloride (1.58 g, 6.06 mmol), phenylcyanamide (2.79 g, 23.6 mmol) and acetonitrile (10 ml) was refluxed for 3 days. The solid product was filtered off. The product was recrystallized from acetonitrile (300 ml). Yield 1.3 g, 57%. M.p. 265-267° C. was refluxed for 3 days The solid product was filtered off The product was recrystallized from acetonitrile (300 ml)