4-Bromobutyronitrile → 4-(5-Methyl-4-imidazolylmethylthio)butyronitrile

HRID 1382765Notes

Reaction equation

HRID 1382765 reaction equation
[Na].[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[CH2:8][SH:9].Br[CH2:11][CH2:12][CH2:13][C:14]#[N:15]>C(O)C>[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[CH2:8][S:9][CH2:11][CH2:12][CH2:13][C:14]#[N:15]

Participants

5

Reactant 3

HCID 214124-BromobutyronitrileHCID 5360545SodiumHCID 13373992(5-Methyl-1H-imidazol-4-yl)methanethiol

Product 1

HCID 212732904-(5-Methyl-4-imidazolylmethylthio)butyronitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (5.0 g) was dissolved in ethanol (300 ml) and 5-methyl-4-(mercaptomethyl)imidazole (17 g) added, followed by a solution of 4-bromobutyronitrile (16 g) in ethanol (50 ml). The mixture was stirred under reflux for 45 minutes, cooled, filtered and the filtrate evaporated to dryness. The residue was taken up in water and extracted with ethyl acetate. The extract was dried (MgSO4) and solvent removed. Recrystallisation of the product from ethanol-ether gave 4-(5-methyl-4-imidazolylmethylthio)butyronitrile as its hydrochloride salt (12 g).

Workup

  1. temperatureunder reflux for 45 minutes
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (MgSO4) and solvent
  7. customremoved
  8. customRecrystallisation of the product from ethanol-ether

Sources & evidence

ORD record
ord-230baa72ed0249c6a3803a7cfa090eb6
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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