Chloromethyl ethyl ether → HCID 18671028, compound

HRID 1057255Notes

Reaction equation

HRID 1057255 reaction equation
[I:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[CH2:22]([O:24][CH2:25]Cl)[CH3:23]>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:22]([O:24][CH2:25][N:6]1[CH:7]=[C:2]([I:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])[CH3:23]

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 696725-IodouracilHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 18671028HCID 18671028, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane, 4.76 g (20 mmol) of 5-iodouracil was suspended and added with 11 ml (45 mmol) of bistrimethylsilylacetamide and stirred for 15 minutes at room temperature to form a homogeneous solution. This solution was added with 2.04 ml (22 mmol) of chloromethyl ethyl ether and 60 mg of tetra-n-butylammonium iodide and heated under reflux for 3 hours. After the solvent was evaporated under reduced pressure, the residue was added with water to produce crystals, which were taken by filtration. The crystals were washed by suspending them in hot methanol and recovering them by cooling and filtration to obtain 5.43 g of 1-(ethoxy-methyl)-5-iodouracil.

Workup

  1. customto form a homogeneous solution
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. customAfter the solvent was evaporated under reduced pressure
  5. additionthe residue was added with water
  6. customto produce crystals, which
  7. filtrationwere taken by filtration
  8. washThe crystals were washed
  9. customrecovering them
  10. temperatureby cooling
  11. filtrationfiltration

Sources & evidence

ORD record
ord-804d1f9517144aa2abcf18cdb8b3c667
Source dataset
uspto-grants-2003_02
Patent number
USRE037979E1

Reaction notes

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