Glycine → Tegafur

HRID 127698Notes

Reaction equation

HRID 127698 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.NCC(O)=O.[O:15]1[CH:19]=[CH:18][CH2:17][CH2:16]1>CN(C)C=O>[O:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

5

Reactant 3

HCID 750GlycineHCID 33855-FluorouracilHCID 709342,3-Dihydrofuran

Product 1

HCID 5386Tegafur

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

In 20 ml of dimethylformamide were dissolved 1.3 g of 5-fluorouracil and 0.75 g of glycin. 2.8 Grams of 2,3-dihydrofuran in several portions were added in 8 hours to the solution while heating it at 145° C. The mixture was then reacted for 5 hours at the same temperature. After completion of the reaction, the reaction liquid was treated in the same manner as described in Example 16. 0.9 g of 1-(2-tetrahydrofuryl)-5-fluorouracil was obtained and 1.0 g of 5-fluorouracil containing 0.75 g of glycin was recovered. The yield of the end product was 56% based on the consumed 5-fluorouracil.

Workup

  1. customThe mixture was then reacted for 5 hours at the same temperature
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. additionwas treated in the same manner

Sources & evidence

ORD record
ord-57e2d231bfbd4bbb82d5a99863bf573c
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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