1,3-Dibromo-5,5-dimethylhydantoin → 4-Pyridinamine,3-bromo-N-methyl-(9CI)

HRID 1975946Notes

Reaction equation

HRID 1975946 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

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 1230984-(Methylamino)pyridine

Product 1

HCID 130982014-Pyridinamine,3-bromo-N-methyl-(9CI)Yield 112.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. customThe solvent was removed
  2. dissolutionthe residue was re-dissolved in ethyl acetate
  3. washThe organic phase was washed four times with saturated sodium carbonate solution
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. 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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