methyl N-[(2-aminophenyl)carbamothioyl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Methyl 4-(o-aminophenyl)-3-thioallophanate is prepared by dissolving 11.7 parts of methoxycarbonyl isothiocyanate in 50 parts of benzene and adding this to 10.8 parts of o-phenylenediamine in 200 parts of benzene at 10°-15° C. After stirring for 1 hour at room temperature, 13.7 parts of methyl 4-(aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D). 13.7 parts of methyl 4-(aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D)

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

Procedure: Methyl 4-(o-aminophenyl)-3-thioallophanate is prepared by dissolving 11.7 parts of methoxycarbonyl isothiocyanate in 50 parts of benzene and adding this to 10.8 parts of o-phenylenediamine in 200 parts of benzene at 10° - 15°C. After stirring for one hour at room temperature, 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187°C.(D). 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187°C.(D)

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

Procedure: Methyl 4-(o-aminophenyl)-3thioallophanate is prepared by dissolving 11.7 parts of methoxycarbonyl isothiocyanate in 50 parts of benzene and adding this to 10.8 parts of o-phenylenediamine in 200 parts of benzene at 10°-15° C. After stirring for 1 hour at room temperature, 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D). 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D)

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

Procedure: Methyl 4-(o-aminophenyl)-3-thioallophanate is prepared by dissolving 11.7 parts of methoxycarbonyl isothiocyanate in 50 parts of benzene and adding this to 10.8 parts of o-phenylenediamine in 200 parts of benzene at 10°-15° C. After stirring for 1 hour at room temperature, 13.7 parts of methyl 4-(aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D). 13.7 parts of methyl 4-(aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D)

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

Procedure: Methyl 4-(o-aminophenyl)-3-thioallophanate is prepared by dissolving 11.7 parts of methoxycarbonyl isothiocyanate in 50 parts of benzene and adding this to 10.8 parts of o-phenylenediamine in 200 parts of benzene at 10°-15° C. After stirring for 1 hour at room temperature, 13.7 parts of methyl 4-(aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D). 13.7 parts of methyl 4-(aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187° C.(D)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 11.7 Parts of methoxycarbonylisothiocyanate is dissolved in 50 parts of benzene and is added to a suspension of 10.8 parts of o-phenylenediamine suspended in 200 parts of benzene at 10°-15°C. The mixture is stirred for 1 hour at room temperature and the product is then removed by filtration yielding 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate, m.p. 182°-183° (D). The melting point is raised to 186°-187° (D) after recrystallization from acetonitrile. the product is then removed by filtration

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

Procedure: A mixture of 1-methoxycarbonyl-3-(2-aminophenyl)thiourea (10.9 g., 0.048 mole), maleic anhydride (4.7 g; 0.048 mole) and ethanol (200 ml) was boiled under reflux with stirring for one hour. The clear solution was allowed to cool and the crystals which deposited were filtered off. These were recrystallised once from ethanol and once from a mixture of acetone and petroleum spirit (b.p. 60°-80° C.) to give 1-methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thiourea (4.4 g) m.p. 170°-173° C. (with decomposition). under reflux to cool the crystals which deposited were filtered off These were recrystallised once from ethanol and once from a mixture of acetone and petroleum spirit (b.p. 60°-80° C.)

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

Procedure: A suspension of 1-methoxycarbonyl-3-(2-aminophenyl)thiourea (9.00 g) in toluene (80 ml) was treated with chloroacetyl chloride (4.52 g) at room temperature and the mixture was heated to reflux for 1 hour with stirring. The mixture was then cooled to room temperature and the resultant white solid was filtered off and recrystallised from ethanol to give 1-methoxycarbonyl-3-(2-chloroacetamidophenyl)thiourea (7.98 g ), m.p. 156°-158° C. the mixture was heated to reflux for 1 hour the resultant white solid was filtered off recrystallised from ethanol

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Concentrated hydrochloric acid (3 ml) was added dropwise to a stirred suspension of 1-methoxycarbonyl-3-(2-aminophenyl)thiourea in dry dioxan (75 ml), the temperature of the reaction mixture being maintained at 20°-25° C. during the addition by slight external cooling. The clear solution obtained was stirred for a further 30 minutes at 25° C. during which time a solid separated. This was filtered off, washed with acetone and recrystallised from ethanol to give 1-methoxycarbonyl-3-(2-aminophenyl)thiourea hydrochloride (5.1 g), m.p. 176°-178° C. (with decomposition). the temperature of the reaction mixture being maintained at 20°-25° C. during the addition by slight external cooling The clear solution obtained separated This was filtered off washed with acetone recrystallised from ethanol

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

Procedure: Methyl chloroformate (23.6 g; 0.25 mole) was added dropwise to a stirred suspension of potassium thiocyanate (24.2 g; 0.25 mole) in dry acetonitrile (100 ml). The temperature of the reaction mixture rose spontaneously to 50° C. and stirring was continued for two hours at 45° C. to 50° C. The reaction mixture was then filtered and the clear filtrate was added dropwise during fifteen minutes to a suspension of o-phenylenediamine (27 g; 0.25 mole) in dry acetonitrile (20 ml), the temperature during the addition being maintained between 15° C. and 20° C. by external cooling. When the addition was complete, the reaction mixture was stirred at laboratory temperature for two hours, filtered, and the crude solid product was crystallised from ethanol to give colourless needles of 1-methoxycarbonyl-3-(2-aminophenyl)-thiourea (15.3 g), m.p. 183.5°-184.5° C. (with decomposition). rose spontaneously to 50° C. The reaction mixture was then filtered the temperature during the addition being maintained between 15° C. and 20° C. by external cooling When the addition the reaction mixture was stirred at laboratory temperature for two hours filtered the crude solid product was crystallised from ethanol