Uracil → 5-Iodouracil

HRID 844836Notes

Reaction equation

HRID 844836 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[I:9]Cl>CO>[I:9][C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

4

Reactant 2

HCID 1174UracilHCID 24640Iodine chloride

Product 1

HCID 696725-IodouracilYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of uracil (28.6 mmol, 3.2 g) and iodine monochloride (49.2 mmol, 7.988 g) in methanol (120 mL) was refluxed for 40 hr. The solvent was removed under vacuum and the residue was crystallized from ethanol:water (1:1, 150 mL) and stored in the refrigerator for 3 h. The resulting needles were collected by filtration and were washed with ethanol:water (1:1 mixture, 50 mL), water (30 mL), hexane (30 mL) and then dried in air to obtain 5.47 g (80%) of 5-iodo uracil as a white needles (mp 278-282° C., Lit. 274-276° C., Synthetic communication 1988, 18, 855-867). EI-HRMS m/e calcd for C4H3IN2O2 (M+) 237.9239, found 237.9244.

Workup

  1. temperaturewas refluxed for 40 hr
  2. customThe solvent was removed under vacuum
  3. customthe residue was crystallized from ethanol:water (1:1, 150 mL)
  4. filtrationThe resulting needles were collected by filtration
  5. washwere washed with ethanol:water (1:1 mixture, 50 mL), water (30 mL), hexane (30 mL)
  6. customdried in air

Sources & evidence

ORD record
ord-72e5240351ce419fbb5636e37d86f0c1
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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