Ethylene Glycol → HCID 13057141, compound

HRID 1649118Notes

Reaction equation

HRID 1649118 reaction equation
C[Si]([C:5]1[NH:10][C:9](=[O:11])[N:8]([Si](C)(C)C)[C:7](=[O:16])[C:6]=1[F:17])(C)C.F[C:19]1[C:20](=[O:26])NC(=O)NC=1.[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:29]=1[CH:30]=[O:31].C(O)CO>C(Cl)(Cl)Cl>[OH:26][CH2:20][CH2:19][O:31][CH:30]([N:10]1[CH:5]=[C:6]([F:17])[C:7](=[O:16])[NH:8][C:9]1=[O:11])[C:29]1[C:28]([Cl:27])=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:36]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 33855-FluorouracilHCID 67372,6-DichlorobenzaldehydeHCID 68585259HCID 68585259, compound

Product 1

HCID 13057141HCID 13057141, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bis(trimethylsilyl)-5-fluorouracil prepared from 5-fluorouracil (10 g), and 2-2,6-dichlorophenyl-1,3-dioxolan (32.0 g) which had been prepared from 2,6-dichlorobenzaldehyde and ethylene glycol were subjected to reaction as in Example 10. Following adding chloroform (100 ml), the reaction mixture was washed twice with a cold saturated NaCl aqueous solution, and then aqueous sodium bicarbonate, and water, and dried over anhydrous magnesium sulfate. The solvent was evaporated off and the residue was purified by column chromatography using silica gel and acetone-chloroform (1:4) as an eluant to give 6.9 g of crystalline 1-[α-(2-hydroxyethoxy)-2,6-dichlorobenzyl]-5-fluorouracil.

Workup

  1. customwere subjected to reaction as in Example 10
  2. washthe reaction mixture was washed twice with a cold saturated NaCl aqueous solution
  3. dry with materialaqueous sodium bicarbonate, and water, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated off
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6c67852ac73545f5ac9b8846d7a55974
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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