Oxalyl dihydrazide

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

Procedure: Two moles of phthalic anhydride (296 g.) and one mole of oxalic dihydrazide (118 g.) in 500 ml. dimethyl sulfoxide and 750 ml. toluene were heated at reflux until two moles of water were removed (about 2 hours). The mixture was cooled and filtered. After washing with benzene, the white product was dried to constant weight at 50° C giving an essentially quantitative yield of N,N'bis(phthalimido)oxamide #-# dimethyl sulfoxide 1:2 complex. were removed (about 2 hours) The mixture was cooled filtered After washing with benzene the white product was dried to constant weight at 50° C

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

Procedure: Two moles of phthalic anhydride (296 g.) and one mole of oxalic dihydrazide (118 g.) in 500 ml. N-methyl-2-pyrrolidone and 500 ml. toluene were heated at reflux until two moles of water were removed (about 2 hours). The mixture was diluted with benzene and filtered. After washing with benzene, the white product was dried to constant weight at 50° C giving an essentially quantitative yield of N,N'-bis(phthalimido)oxamide-N-methyl-2-pyrrolidone 1:2 complex. were removed (about 2 hours) The mixture was diluted with benzene filtered After washing with benzene the white product was dried to constant weight at 50° C

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

Procedure: Two moles (200 g.) of succinic anhydride and one mole (118 g.) of oxalic dihydrazide in 750 ml. N-methyl-2-pyrrolidone and 500 ml. toluene were heated at reflux until water evolution was complete (about 4 hours). Upon cooling, a crystalline complex separated. The mixture was diluted with benzene and then filtered. After drying at 50° C, the complex was treated with water to give N,N'-bis(succinimido)oxamide, having a melting point of >310° C. The overall yield was about 49%. (about 4 hours) Upon cooling a crystalline complex separated The mixture was diluted with benzene filtered After drying at 50° C the complex was treated with water

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

Procedure: Two moles (200 g.) of succinic anhydride and one mole (118 g.) of oxalic dihydrazide in 750 ml. N-methyl-2-pyrrolidone and 500 ml. toluene were heated at reflux until water evolution was complete (about 4 hours). Upon cooling, a crystalline complex separated. The mixture was diluted with benzene and then filtered. After drying at 50° C, the complex was treated with water to give N,N'-bis(succinimido)oxamide, having a melting point of >310° C. The overall yield was about 49%. (about 4 hours) Upon cooling a crystalline complex separated The mixture was diluted with benzene filtered After drying at 50° C the complex was treated with water

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

Procedure: Two moles of phthalic anhydride (296g) and one mole of oxalic dihydrazide (118 g) in xylene (2.5 l) were heated at reflux until two moles of water were removed (about 24 hours). The product was filtered and dried at 50° C. N,N'-bis(phthalimido)-oxamide was obtained in 94-6 percent yield. The compound was a white solid melting at 295° C (dec.) and having the following elemental analysis by weight percent: were removed (about 24 hours) The product was filtered dried at 50° C

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 35.4 g of oxalic acid bis-hydrazide are suspended in 1000 ml of dimethyl acetamide, the suspension is briefly heated to 100° C and cooled to room temperature, and 93.5 g of salicylic acid chloride are slowly added in such a way that the reaction temperature does not exceed 40° C. After a further 15 minutes' stirring a largely homogeneous, yellowish solution has been obtained. After filtering off the undissolved constituents, the solution is mixed with 1.2 liters of ice water, whereupon the reaction product precipitates. The substance is filtered off, washed with water and purified by again precipitating it from dimethyl acetamide solution by means of water. After isolation and intensive drying at 130° C in vacuo, N,N'-bis-(salicyloyl)-oxalic acid dihydrazide (Stabiliser No. 2) is obtained as a white powder of melting point>320° C (decomposition). cooled to room temperature does not exceed 40° C has been obtained After filtering off the undissolved constituents the solution is mixed with 1.2 liters of ice water, whereupon the reaction product precipitates The substance is filtered off washed with water purified by again precipitating it from dimethyl acetamide solution by means of water After isolation and intensive drying at 130° C in vacuo

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 35.4 g of oxalic acid bis-hydrazide are suspended in 1000 ml of dimethyl acetamide, the suspension is briefly heated to 100° C and cooled to room temperature, and 93.5 g of salicylic acid chloride are slowly added in such a way that the reaction temperature does not exceed 40° C. After a further 15 minutes' stirring a largely homogeneous, yellowish solution has been obtained. After filtering off the undissolved constituents, the solution is mixed with 1.2 liters of ice water, whereupon the reaction product precipitates. The substance is filtered off, washed with water and purified by again precipitating it from dimethyl acetamide solution by means of water. After isolation and intensive drying at 130° C in vacuo, N,N'-bis-(salicyloyl)-oxalic acid dihydrazide (Stabiliser No. 2) is obtained as a white powder of melting point>320° C (decomposition). cooled to room temperature does not exceed 40° C has been obtained After filtering off the undissolved constituents the solution is mixed with 1.2 liters of ice water, whereupon the reaction product precipitates The substance is filtered off washed with water purified by again precipitating it from dimethyl acetamide solution by means of water After isolation and intensive drying at 130° C in vacuo

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

Procedure: Two moles of phthalic anhydride (296 g.) and one mole of oxalic dihydrazide (118 g.) in 500 ml. dimethyl sulfoxide and 750 ml. toluene were heated at reflux until two moles of water were removed (about two hours). The mixture was cooled and filtered. After washing with benzene, the white product was dried to constant weight at 50° C. giving an essentially quantitative yield of N,N'bis(phthalimido)oxamide-dimethyl sulfoxide 1:2 complex. were removed (about two hours) The mixture was cooled filtered After washing with benzene the white product was dried to constant weight at 50° C.

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

Procedure: Two moles of phthalic anhydride (296 g.) and one mole of oxalic dihydrazide (118 g.) in 500 ml. N-methyl-2-pyrrolidone and 500 ml. toluene were heated at reflux until two moles of water were removed (about two hours). The mixture was diluted with benzene and filtered. After washing with benzene, the white product was dried to constant weight at 50° C. giving an essentially quantitative yield of N,N'-bis(phthalimido)oxamide-N-methyl-2-pyrrolidone 1:2 complex. were removed (about two hours) The mixture was diluted with benzene filtered After washing with benzene the white product was dried to constant weight at 50° C.

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

Procedure: Two moles (200 g.) of succinic anhydride and one mole (118 g.) of oxalic dihydrazide in 750 ml. N-methyl-2-pyrrolidone and 500 ml. toluene were heated at reflux until water evolution was complete (about four hours). Upon cooling, a crystalline complex separated. The mixture was diluted with benzene and then filtered. After drying at 50° C., the complex was treated with water to give N,N'-bis(succinimido)oxamide, having a melting point of >310° C. The overall yield was about 49%. (about four hours) Upon cooling a crystalline complex separated The mixture was diluted with benzene filtered After drying at 50° C. the complex was treated with water

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

Procedure: Two moles of phthalic anhydride (296 g) and one mole of oxalic dihydrazide (118 g) in xylene (2.5 l) were heated at reflux until two moles of water were removed (about 24 hours). The product was filtered and dried at 50° C. N,N'-bis(phthalimido)oxamide was obtained in 94-6 percent yield. The compound was a white solid melting at 295° C. (dec.) and having the following elemental analysis by weight percent: were removed (about 24 hours) The product was filtered dried at 50° C

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

Procedure: Two moles of phthalic anhydride (296 g.) and one mole of oxalic dihydrazide (118 g.) in 500 ml. dimethyl sulfoxide and 750 ml. toluene were heated at reflux until two moles of water were removed (about 2 hours). The mixture was cooled and filtered. After washing with benzene, the white product was dried to constant weight at 50° C giving an essentially quantitative yield of N,N'bis(phthalimido)oxamide #-# dimethyl sulfoxide 1:2 complex. were removed (about 2 hours) The mixture was cooled filtered After washing with benzene the white product was dried to constant weight at 50° C