Acetic Anhydride → HCID 4443484, compound

HRID 1649102Notes

Reaction equation

HRID 1649102 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[C:12]([F:14])[C:10](=[O:11])[NH:9][C:7]1=[O:8].[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[C:12]([F:14])[C:10](=[O:11])[NH:9][C:7]1=[O:8])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 723595-Fluoro-1-((2-hydroxyethoxy)methyl)uracil

Product 1

HCID 4443484HCID 4443484, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2-Hydroxyethoxy)methyl-5-fluorouracil (1 g) prepared in Example 1 was dissolved in a mixture of acetic anhydride (5 ml) and pyridine (5 ml) and the solution was stirred at room temperature for 3 hours. The reaction mixture was poured into ice-water and the resulting oil was extracted with chloroform (30 ml). The extract was washed with hydrochloric acid, aqueous sodium bicarbonate and then water, dried over magnesium sulfate and the solvent was evaporated off under reduced pressure. The residue was treated with methanol to give 0.9 g of crystalline 1-(2-acetoxyethoxy)methyl-5-fluorouracil.

Workup

  1. extractionthe resulting oil was extracted with chloroform (30 ml)
  2. washThe extract was washed with hydrochloric acid, aqueous sodium bicarbonate
  3. dry with materialwater, dried over magnesium sulfate
  4. customthe solvent was evaporated off under reduced pressure
  5. additionThe residue was treated with methanol

Sources & evidence

ORD record
ord-047280dd125c4660b11df68ffc118970
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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