N-bromobutanimide → 5-Amino-1-benzyl-2-bromo-1H-imidazole-4-carbonitrile

HRID 1989806Notes

Reaction equation

HRID 1989806 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[N:12][C:11]=1[C:22]#[N:23]>O1CCCC1>[NH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([Br:1])=[N:12][C:11]=1[C:22]#[N:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3432245-Amino-1-benzyl-1H-imidazole-4-carbonitrile

Product 1

HCID 216688075-Amino-1-benzyl-2-bromo-1H-imidazole-4-carbonitrileYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-bromosuccinimide (3.55 g, 19.9 mmol) was added portionwise to a suspension of 5-amino-1-benzyl-1H-imidazole-4-carbonitrile (3.59 g, 18.1 mmol) in tetrahydrofuran (50 ml) and the reaction mixture stirred at room temperature for 10 minutes. The solvent was evaporated in vacuo and the residue extracted from a saturated aqueous solution of sodium hydrogen carbonate (50 ml) into ethyl acetate (300 ml), dried over magnesium sulphate, filtered and evaporated in vacuo. The crude material was purified by column chromatography over silica gel eluting with 2-3% dichloromethane:methanol. The material was recrystalised from ethyl acetate, then triturated with diethyl ether to yield the title compound as a pink solid (2.7 g, 9.7 mmol, 53%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionthe residue extracted from a saturated aqueous solution of sodium hydrogen carbonate (50 ml) into ethyl acetate (300 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude material was purified by column chromatography over silica gel eluting with 2-3% dichloromethane
  7. customThe material was recrystalised from ethyl acetate
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-e267e3ae1f604395837f4ad5faceef39
Source dataset
uspto-grants-2010_01
Patent number
US07642350B2

Reaction notes

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