Water → HCID 23468997, compound

HRID 128242Notes

Reaction equation

HRID 128242 reaction equation
[N:1]1([CH2:6][C:7]2[NH:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:12](#[N:15])[CH:13]=[CH2:14].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O>O1CCOCC1>[C:12]([CH2:13][CH2:14][N:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 23469000HCID 23469000, compound

Product 1

HCID 23468997HCID 23468997, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(Imidazol-1-ylmethyl)pyrrole (4.41 g) and acrylonitrile (6.0 ml) were dissolved in dioxan (75 ml) and benzyltrimethylammonium hydroxide (1.5 ml of 40% solution in methanol) was added. The mixture was warmed to 55° for 1 hour and then allowed to stand at room temperature for 18 hours. It was then poured into water and the mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform gave 1-(2-cyanoethyl)-2-(imidazol-1-ylmethyl)pyrrole (5.0 g) as an oil.

Workup

  1. temperatureThe mixture was warmed to 55° for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customwas chromatographed on silica gel
  8. washElution with chloroform

Sources & evidence

ORD record
ord-afbc4c15210947ee82f96029ef2132f0
Source dataset
uspto-grants-1981_03
Patent number
US04259345

Reaction notes

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