Tetrahydrofuran → HCID 20266525, compound

A mixture of about 4.71 g of 5-nitro-2-furoic acid, about 4.86 g of 1,1'-carbonyldiimidazole and about 100 ml of dry tetrahydrofuran was stirred in a 250 ml round bottom flask with a drying tube for about 3 hours. An approximately 4.0 g portion of 1H-1,2,4-triazole-1-propanamine was added and the mixture was stirred overnight at room temperature. The mixture was refluxed for about 3 hours, about 15 ml of water was added, refluxing continued for about 2 hours, then the mixture was concentrated to remove the solvents. An approximately 200 ml portion of methylene chloride and about 30 ml of 1N sodium hydroxide were added, the mixture was shaken and the organic layer separated and washed with two about 50 ml portions of water, then dried, filtered and evaporated to a solid. This solid was recrystallized from ethanol, giving about 290 mg of the desired product as beige crystals, mp 176°-177° C.

1. stirringthe mixture was stirred overnight at room temperature
2. temperatureThe mixture was refluxed for about 3 hours
3. temperaturerefluxing
4. waitcontinued for about 2 hours
5. concentrationthe mixture was concentrated
6. customto remove the solvents
7. additionAn approximately 200 ml portion of methylene chloride and about 30 ml of 1N sodium hydroxide were added
8. stirringthe mixture was shaken
9. customthe organic layer separated
10. washwashed with two about 50 ml portions of water
11. customdried
12. filtrationfiltered
13. customevaporated to a solid
14. customThis solid was recrystallized from ethanol

ORD record

ord-aa3a69444f59481bb79df53fdeeb6a3a

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04542145