Iodine chloride → E-5-(2-iodovinyl)uracil
Reaction equation
[CH:1]([C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1)=[CH2:2].[I:11]Cl>CN(C)C=O>[I:11]/[CH:2]=[CH:1]/[C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-vinyluracil (1.1 g, 8 mmoles) was dissolved in dry dimethylformamide (40 ml). To this solution was added a solution of iodine monochloride (1.28 g, 8 mmoles) in dry dimethylformamide (20 ml). The reaction mixture was allowed to stand, with occasional shaking, for 30 minutes and then heated at 100° for 30 minutes. The solution was then evaporated under reduced pressure to a brown oil to which was added water (20 ml). The resulting dark brown suspension was filtered and the brown solid collected and dried giving crude E-5-(2-iodovinyl)uracil (1.6 g, 76% yield). For the next stage this was not purified further.
Workup
- temperatureheated at 100° for 30 minutes
- customThe solution was then evaporated under reduced pressure to a brown oil to which
- additionwas added water (20 ml)
- filtrationThe resulting dark brown suspension was filtered
- customthe brown solid collected
- customdried
Sources & evidence
- ORD record
- ord-89d54d9abebe4dd0930d7261c8e750bf
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04424211
Reaction notes
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