Nicotinic Acid → Tegafur
Reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10]([OH:18])(=O)[C:11]1[CH:16]=[CH:15]C=NC=1.O1C=CCC1>CN(C)C=O>[O:18]1[CH2:10][CH2:11][CH2:16][CH:15]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
In 30 ml of dimethylformamide were dissolved 2.6 g of 5-fluorouracil and 0.246 g of nicotinic acid. 2.8 Grams of 2,3-dihydrofuran in several portions were added in 4 hours to the solution while heating it at 140° C. The mixture was then reacted for 4 hours at the same temperature. After completion of the reaction, dimethylformamide was distilled off from the reaction liquid and 50 ml of chloroform were added to the residue. After stirring, the solution was filtered to remove insoluble matters and the filrate was washed with water and dried over anhydrous sodium sulfate. Then, chloroform was distilled off from the dried filtrate to obtain 1.85 g of 1-(2-tetrahydrofuryl)-5-fluorouracil which had a melting point of 165°-168° C. The chloroform insoluble matters were 5-fluorouracil containing 0.24 g of nicotinic acid. The yield of the end product was 61% based on the consumed 5-fluorouracil.
Workup
- customThe mixture was then reacted for 4 hours at the same temperature
- distillationwas distilled off from the reaction liquid and 50 ml of chloroform
- additionwere added to the residue
- filtrationthe solution was filtered
- customto remove insoluble matters
- washthe filrate was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThen, chloroform was distilled off from the dried filtrate
Sources & evidence
- ORD record
- ord-3b230358e8764413b85a7c0bf5d808ce
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256885
Reaction notes
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