4-Toluenesulfonyl chloride → HCID 13057119, compound

HRID 1649103Notes

Reaction equation

HRID 1649103 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]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]2[CH:13]=[C:12]([F:14])[C:10](=[O:11])[NH:9][C:7]2=[O:8])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 723595-Fluoro-1-((2-hydroxyethoxy)methyl)uracil

Product 1

HCID 13057119HCID 13057119, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2-Hydroxyethoxy)methyl-5-fluorouracil (1 g) obtained in Example 1 was dissolved in pyridine (5 ml) and to the solution was added p-toluenesulfonylchloride (1.12 g) under cooling in an ice bath, and then the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the mixture was poured into ice-water and the resulting oil was extracted with chloroform (30 ml). The chloroform layer was washed with hydrochloric acid and then with water, and dried over magnesium sulfate to give crystalline 1-(2-p-toluenesulfonyloxyethoxy)methyl-5-fluorouracil (1.2 g).

Workup

  1. temperatureunder cooling in an ice bath
  2. customAfter completion of the reaction
  3. extractionthe resulting oil was extracted with chloroform (30 ml)
  4. washThe chloroform layer was washed with hydrochloric acid
  5. dry with materialwith water, and dried over magnesium sulfate

Sources & evidence

ORD record
ord-cb2488492cc447348635518e0449408c
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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