methyl N-(oxomethylidene)carbamate

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

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: To a solution of methoxycarbonylisocyanate (3.78 g. 0.0374 mole) in 45 ml. of dioxane is added 4-aminoveratrole (5.73 g., 0.037 mole) while maintaining a temperature of 20°-30°. After completing the addition, another 45 ml. portion of dioxane is added and the mixture then heated at reflux for a period of one hour. Evaporation of the solvent and crystallization of residual material from nitromethane provides analytically pure 1-(3,4-dimethoxyphenyl)-3-methoxycarbonylurea, m.p. 168°-170°. while maintaining a temperature of 20°-30° the addition the mixture then heated at reflux for a period of one hour Evaporation of the solvent and crystallization of residual material from nitromethane

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

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

Procedure: To 4-nitrobenzenesulfonamide (2.1 grams, 0.01 mole) in 100 milliliters dry toluene was added 1.2 grams (0.012 mole) methoxycarbonyl isocyanate. Three drops of pyridine were added. The mixture was refluxed for four hours. After cooling the precipitate was filtered off and washed with toluene. The solid material was dried. There was obtained 2.4 grams of the title compound, m.p. 150°-158° C. The mixture was refluxed for four hours After cooling the precipitate was filtered off washed with toluene The solid material was dried

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

Procedure: One part by weight of methoxycarbonyl isocyanate was added gradually with stirring to a solution of 2 parts by weight of 2-amino-5-chlorobenzothiazole in 100 parts by weight of methylene chloride and 50 parts by weight of ethyl ether. After stirring the reaction mixture at room temperature overnight, a product was isolated by filtration giving an 85% yield of methyl 4-(5-chlorobenzothiazol-2-yl)allophanate having a melting point of 395°. a product was isolated by filtration

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

Procedure: A solution of 2 parts by weight of methoxycarbonylisocyanate in 15 parts by weight of methylene chloride was added gradually with stirring to a solution, at room temperature, of 4 parts by weight of 2-amino-5-chloro-4-methylbenzothiazole in 75 parts by weight of methylene chloride and 50 parts by weight of tetrahydrofuran. After stirring the reaction mixture at room temprature overnight, a product was isolated by filtration giving a 40% yield of methyl 4-(5-chloro-4-methylbenzothiazol-2-yl)allophanate having a melting point greater than 275° . a product was isolated by filtration

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

Procedure: Two and one half parts by weight of methoxycarbonyl isocyanate was added gradually with stirring to a solution of 4 parts by weight of 2-amino-4-methylbenzothiazole dissolved in 250 parts by weight of methylene chloride. The reaction mixture was stirred at room temperature for 12 hours. The solution was concentrated to one fifth the original volume and the solid isolated by filtration to give a 37% yield of methyl 4-(4-methylbenzothiazol-2-yl)allophanate having a melting point of 272°-280° with decomposition. The solution was concentrated to one fifth the original volume the solid isolated by filtration

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

Procedure: Three and one half parts by weight of methoxycarbonyl isocyanate was added gradually with stirring to a solution at room temperature of 41/2 parts by weight of 2-aminobenzothiazole dissolved in 150 parts by weight of methylene chloride. After stirring the reaction mixture at room temperature for 12 hours, the product was isolated by filtration giving a 40% yield of essentially pure methyl 4-(benzothiazol-2-yl)allophanate having a melting point of 338°-340° C with decomposition. the product was isolated by filtration

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

Procedure: Five and one half parts by weight of methoxycarbonyl isocyanate was added gradually with stirring to a solution at room temperature of nine parts by weight of 2-amino-4-chlorobenzothiazole dissolved in 200 parts by weight of dioxane. After stirring the reaction mixture at room temperature overnight, a product was isolated by filtration giving a 45% yield of methyl 4-[4-chlorobenzothiazol-2-yl]allophanate having a melting point of 319°-20° C. a product was isolated by filtration

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

Procedure: To a solution of methoxycarbonylisocyanate (3.78 g. 0.0374 mole) in 45 ml. of dioxane is added 4-aminoveratrole (5.73 g., 0.037 mole) while maintaining a temperature of 20°-30°. After completing the addition, another 45 ml. portion of dioxane is added and the mixture then heated at reflux for a period of one hour. Evaporation of the solvent and crystallization of residual material from nitromethane provides analytically pure 1-(3,4-dimethoxyphenyl)-3-methoxycarbonylurea, m.p. 168°-170°. while maintaining a temperature of 20°-30° the addition the mixture then heated at reflux for a period of one hour Evaporation of the solvent and crystallization of residual material from nitromethane