1-(1H-Imidazol-1-yl)ethanone → HCID 23347409, compound

HRID 1856008Notes

Reaction equation

HRID 1856008 reaction equation
[N:1]1([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:16](N1C=CN=C1)(=[O:18])[CH3:17]>>[C:16]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:8]1)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 7924863-(imidazol-1-ylmethyl)-1H-indole

Product 1

HCID 23347409HCID 23347409, compoundYield 42.5%

Procedure

A mixture consisting of 3-(imidazol-1-ylmethyl)indole (0.97 g) and 1-acetylimidazole (1.10 g) was heated on a steam bath for a period of 3.5 hours to give an orange oil, which soon solidied on cooling. The resulting solid product was then chromatographed on silica gel. Elution with chloroform first gave some minor impurity, followed by the pure product. The product-containing fractions were then combined and subsequently evaporated to dryness while under reduced pressure to afford a solid residue, which was thereafter crystallized from ethyl acetate to yield pure 1-acetyl-3-(imidazol-1-ylmethyl)indole (yield, 0.50 g.), m.p. 122° C.

Workup

  1. temperaturewas heated on a steam bath for a period of 3.5 hours
  2. customto give an orange oil, which
  3. temperatureon cooling
  4. customThe resulting solid product was then chromatographed on silica gel
  5. washElution with chloroform
  6. customfirst gave some minor impurity
  7. customsubsequently evaporated to dryness while under reduced pressure
  8. customto afford a solid residue, which
  9. customwas thereafter crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8854147abbd941e4953808eb4891f5bc
Source dataset
uspto-grants-1980_08
Patent number
US04217357

Reaction notes

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