2-Methylimidazole → HCID 20260627, compound

HRID 1583409Notes

Reaction equation

HRID 1583409 reaction equation
[OH-].[Na+].Br[CH2:4][CH2:5][CH2:6][C:7]#[N:8].[CH3:9][C:10]1[NH:11][CH:12]=[CH:13][N:14]=1>O.CN(C)C=O>[CH3:9][C:10]1[N:11]([CH:6]([CH2:5][CH3:4])[C:7]#[N:8])[CH:12]=[CH:13][N:14]=1

Participants

6

Reactant 3

HCID 127492-MethylimidazoleHCID 14798Sodium HydroxideHCID 214124-Bromobutyronitrile

Product 1

HCID 20260627HCID 20260627, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

12.8 g of sodium hydroxide was dissolved in 12 ml of water and diluted with 150 ml of dimethylformamide containing 20.3 g of 2-methylimidazole. A solution of 50.0 g of 4-bromobutyronitrile in 100 ml of dimethylformamide was added slowly maintaining the temperature below 30° C. The resulting mixture was stirred overnight and was concentrated. The residue was taken up in 150 ml of brine and extracted with dichloromethane. The combined organic layers were dried over potassium carbonate and evaporated. The product was distilled. The early fractions were mostly 2-methylimidazole and were discarded. The main fraction 23.2 g, bp 160°-185° C./2.5 mm, was redistilled to give 14.7 g (31%) of (2-methyl-1H-imidazol-1-yl)-butanitrile, bp 140°-147° C./0.5 mm.

Workup

  1. temperaturemaintaining the temperature below 30° C
  2. concentrationwas concentrated
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over potassium carbonate
  5. customevaporated
  6. distillationThe product was distilled
  7. distillationThe main fraction 23.2 g, bp 160°-185° C./2.5 mm, was redistilled
  8. customto give 14.7 g (31%) of (2-methyl-1H-imidazol-1-yl)-butanitrile, bp 140°-147° C./0.5 mm

Sources & evidence

ORD record
ord-b9a23861d94a4259b7908c0c11f6d2e9
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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