Triethylamine → HCID 178467223, compound

HRID 280745Notes

Reaction equation

HRID 280745 reaction equation
Br[C:2](=[CH:6]OC)[C:3](=[O:5])[CH3:4].Cl.[C:10]([NH2:13])(=[NH:12])[CH3:11].C(N(CC)CC)C>O1CCCC1>[CH3:11][C:10]1[NH:12][CH:6]=[C:2]([C:3](=[O:5])[CH3:4])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67170Acetamidine monohydrochlorideHCID 54475692HCID 54475692, compound

Product 1

HCID 178467223HCID 178467223, compoundYield 230%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.3 g (35 mmol) of 3-bromo-4-methoxy-3-buten-2-one, 16.7 g acetamidine hydrochloride (175 mmol) and 29.2 ml triethylamine (210 mmol) were combined in 300 ml tetrahydrofuran and heated at reflux for 6 hours. The solvent was removed in vacuo to a crude orange solid. The crude solid was dissolved in 200 ml ethyl acetate and concentrated to 25 ml by boiling off the solvent. Cooling in ice resulted in crystallization of a yellow solid. This was collected by filtration, washed first with ethyl acetate, then with ether and dried at 25° in vacuo to give 9.995 g (23%) of 1-(2-methyl-4-imidazolyl)ethanone, mp 124°-7°. nmr (DMSO-d6) (δ): 4.61 (s, 1H); 1.41 (s, 3H); 1.39 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was removed in vacuo to a crude orange solid
  4. dissolutionThe crude solid was dissolved in 200 ml ethyl acetate
  5. concentrationconcentrated to 25 ml
  6. temperatureCooling in ice
  7. customresulted in crystallization of a yellow solid
  8. filtrationThis was collected by filtration
  9. washwashed first with ethyl acetate
  10. dry with materialwith ether and dried at 25° in vacuo

Sources & evidence

ORD record
ord-a42a9f2f867e488b95034ac7eb1b3626
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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