1,3-Dibromo-5,5-dimethylhydantoin → 3-bromo-N-methylpyridin-4-amine
Reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Br:9]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[Br:9][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[NH:2][CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 10.6 g (98 mmol) 4-(N-methylamino)-pyridine in 200 ml tetrahydrofuran was added dropwise a solution of 14.0 g (49 mmol) 1,3-dibromo-5,5-dimethylhydantoin in 50 ml tetrahydrofuran at room temperature within 1.5 h. The solvent was removed and the residue was re-dissolved in ethyl acetate. The organic phase was washed four times with saturated sodium carbonate solution, dried (sodium sulfate) and evaporated. The residue was purified by flash chromatography to give 10.3 g (56%) of the title compound as white crystals.
Workup
- customThe solvent was removed
- dissolutionthe residue was re-dissolved in ethyl acetate
- washThe organic phase was washed four times with saturated sodium carbonate solution
- dry with materialdried (sodium sulfate)
- customevaporated
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-89fe98bd4d8f4af48daafe991e54740f
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225316B1
Reaction notes
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