N-phenylfuran-2-carboxamide

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydro-2-furancarbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 18) at 0°-5°. After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished N,N'-bis[2,3-bis (acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro-2-furanyl)carbonyl]amino]-1,3-benzenedicarboxamide (6.19 g), m.p. 101°-104°. prepared as in part A of Example 18) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydro-2-furancarbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 18) at 0°-5° . After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel prepared as in part A of Example 18) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) (prepared as described in EP 431,838) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydrofuran-2-carbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 3) at 0°-5°. After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished N,N'-bis [2,3-bis (acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro -2-furanyl) carbonyl]amino]-1,3 -benzenedicarboxamide (6.19 g) , m.p. 101°-104°. prepared as in part A of Example 3) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-phenyl furamide was prepared by adding to a mixture of aniline (23.3 g; 250 mmol) and triethylamine (25.3 g; 250 mmol) in dichloromethane slowly 32.6 g (250 mmol) of 2-furoyl chloride, while maintaining the temperature at -10° C. The product obtained was washed with diluted hydrochloric acid and water, dried with magnesium sulphate and evaporated. The product so obtained was than triturated with hexane and filtered. 39.3 g (84% yield of product was recovered. The product obtained was washed with diluted hydrochloric acid and water dried with magnesium sulphate evaporated The product so obtained than triturated with hexane filtered

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-phenyl furamide was prepared by adding to a mixture of aniline (23.3 g; 250 mmol) and triethylamine (25.3 g; 250 mmol) in dichloromethane slowly 32.6 g (250 mmol) of 2-furoyl chloride, while maintaining the temperature at -10° C. The product obtained was washed with diluted hydrochloric acid and water, dried with magnesium sulphate and evaporated. The product so obtained was than triturated with hexane and filtered. 39.3 g (84% yield of product was recovered. The product obtained was washed with diluted hydrochloric acid and water dried with magnesium sulphate evaporated The product so obtained than triturated with hexane filtered

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydro-2-furancarbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 18) at 0°-5°. After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished N,N'-bis[2,3-bis (acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro-2-furanyl)carbonyl]amino]-1,3-benzenedicarboxamide (6.19 g), m.p. 101°-104°. prepared as in part A of Example 18) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydro-2-furancarbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 18) at 0°-5°. After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro-2-furanyl)carbonyl]amino]-1,3-benzenedicarboxamide (6.19 g), m.p. 101°-104°. prepared as in part A of Example 18) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis (acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) (prepared as described in EP 431,838) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydrofuran-2-carbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 3) at 0°-5° . After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40° . The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished N,N'-bis[2,3-bis(acetyloxy)propyl]2,4,6-triiodo-5-[[(tetrahydro-2furanyl)carbonyl]amino]-1,3-benzenedicarboxamide (6.19 g), m.p. 101°-104°. prepared as in part A of Example 3) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydro-2-furancarbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 18) at 0°-5° . After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel prepared as in part A of Example 18) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) (prepared as described in EP 431,838) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydrofuran-2-carbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 3) at 0°-5°. After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished N,N'-bis [2,3-bis (acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro -2-furanyl) carbonyl]amino]-1,3 -benzenedicarboxamide (6.19 g) , m.p. 101°-104°. prepared as in part A of Example 3) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-phenyl furamide was prepared by adding to a mixture of aniline (23.3 g; 250 mmol) and triethylamine (25.3 g; 250 mmol) in dichloromethane slowly 32.6 g (250 mmol) of 2-furoyl chloride, while maintaining the temperature at -10° C. The product obtained was washed with diluted hydrochloric acid and water, dried with magnesium sulphate and evaporated. The product so obtained was than triturated with hexane and filtered. 39.3 g (84% yield of product was recovered. The product obtained was washed with diluted hydrochloric acid and water dried with magnesium sulphate evaporated The product so obtained than triturated with hexane filtered

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

Procedure: To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide (8.73 g, 10 mmol) in N,N-dimethylacetamide (30 mL), was added in drops tetrahydro-2-furancarbonyl chloride (1.8 g, 13 mmol) (prepared as in part A of Example 18) at 0°-5°. After the addition, the mixture was stirred at 0°-5° for 0.5 hour, then at room temperature for 20 hours. Nitrogen gas was purged through the solution for 0.25 hour, and the N,N-dimethylacetamide was removed in vacuo at 40°. The residue was dissolved in ethyl acetate (200 mL), and the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL). After drying over sodium sulfate, the solvent was removed in vacuo to obtain the title B furanilide as an off-white foamy material (9.27 g, crude). The crude product (7.2 g), upon purification by column chromatography over silica gel (mobile phase: hexane/ethyl acetate) furnished N,N'-bis[2,3-bis (acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro-2-furanyl)carbonyl]amino]-1,3-benzenedicarboxamide (6.19 g), m.p. 101°-104°. prepared as in part A of Example 18) at 0°-5° After the addition at room temperature for 20 hours Nitrogen gas was purged through the solution for 0.25 hour the N,N-dimethylacetamide was removed in vacuo at 40° The residue was dissolved in ethyl acetate (200 mL) the solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL) After drying over sodium sulfate the solvent was removed in vacuo