Water → HCID 54544079, compound

HRID 741706Notes

Reaction equation

HRID 741706 reaction equation
[CH3:1][C:2]([CH3:5])([O-])C.[K+].BrCC=C.[CH3:11][N:12]([CH:14]=[N:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)[CH3:13].O>CN(C=O)C>[CH3:11][N:12]([CH:14]=[N:15][C:16]1[N:17]([CH2:1][CH:2]=[CH2:5])[CH:18]=[CH:19][N:20]=1)[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 54387791HCID 54387791, compound

Product 1

HCID 54544079HCID 54544079, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium t-butoxide (0.37 g) and 3-bromo-1-propene (0.3 ml) were added to a solution of 2-(dimethylaminomethylene)aminoimidazole (0.2 g) in DMF (3 ml) under ice-cooling. After warming to room temperature, the mixture was stirred for 30 minutes. Water was added to the reaction mixture, and the product was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (eluent: chloroform-methanol-ammonia water=40:1:0.1) to give 2-(dimethylaminomethylene)amino-1-(2-propenyl)imidazole (0.31 g, Yield: 80%) as a brown oil.

Workup

  1. temperaturecooling
  2. extractionthe product was extracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel (eluent: chloroform-methanol-ammonia water=40:1:0.1)

Sources & evidence

ORD record
ord-ae8601af1f6f45b89720803a8408fcad
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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