5-Fluorouracil → Tegafur

HRID 127696Notes

Reaction equation

HRID 127696 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(N(CC)CC)C.[O:21]1[CH:25]=[CH:24][CH2:23][CH2:22]1>CN(C)C=O>[O:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

6

Reactant 4

HCID 33855-FluorouracilHCID 8471TriethylamineHCID 709342,3-DihydrofuranHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5386TegafurYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of dimethylformamide were dissolved 2.6 g of 5-fluorouracil, 2.66 g of anhydrous aluminum chloride and 7.0 ml of triethylamine. The reaction was carried out at 130° C. for 6 hours while adding 3.0 ml of 2,3-dihydrofuran to the solution. The reaction liquid was treated in the same manner as described in Example 13 to obtain 2.4 g of (1-(2-tetrahydrofuryl)-5-fluorouracil. The yield was 60%.

Workup

  1. customThe reaction liquid
  2. additionwas treated in the same manner

Sources & evidence

ORD record
ord-8add7b5016184751acdafa27bd5230b6
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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