5-Fluorouracil → HCID 20525083, compound

HRID 1702796Notes

Reaction equation

HRID 1702796 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[S:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[N:15]=[C:16]=[O:17]>CN(C)C(=O)C>[S:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[NH:15][C:16]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:17]

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 20525062HCID 20525062, compound

Product 1

HCID 20525083HCID 20525083, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-fluorouracil (2.6 g.) in N,N-dimethylacetoamide (10 ml.) was added to oily 2-tetrahydrothiophenyl isocyanate (3.1 g.). The mixture was stirred at 50° C. for 8 hours and concentrated in vacuo. The residue was treated with water (80 ml.) to give crystalline precipitates, which were collected by filtration and dried over phosphoric anhydride to give 1-[N-(2-tetrahydrothienyl)carbamoyl]-5-fluorouracil (3.68 g.); pale yellow crystalline powder.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with water (80 ml.)
  3. customto give crystalline precipitates, which
  4. filtrationwere collected by filtration
  5. dry with materialdried over phosphoric anhydride

Sources & evidence

ORD record
ord-f0fb89ab656e4fa9a0187bd0ccc9d43b
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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