Tetrahydro-2-furancarbonyl chloride → N-Phenyl-2-furancarboxamide

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°.

1. customprepared as in part A of Example 18) at 0°-5°
2. additionAfter the addition
3. waitat room temperature for 20 hours
4. customNitrogen gas was purged through the solution for 0.25 hour
5. customthe N,N-dimethylacetamide was removed in vacuo at 40°
6. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
7. washthe solution was washed successively with cold aqueous sodium bicarbonate (2×50 mL), water (2×50 mL) and saturated sodium chloride (2×50 mL)
8. dry with materialAfter drying over sodium sulfate
9. customthe solvent was removed in vacuo

ORD record

ord-ae9eb94f5437456c8c0fc612ddb24416

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05591846