Acetic Acid → HCID 18437780, compound

HRID 1643184Notes

Reaction equation

HRID 1643184 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:6]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH3:4].[C:22](O)(=[O:24])C>C=O>[CH2:1]([N:5]1[C:9]([CH2:22][OH:24])=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:7]=[C:6]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18437783HCID 18437783, compound

Product 1

HCID 18437780HCID 18437780, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

1-Butyl-2,4-diphenylimidazole (3 g)is dissolved in 50 ml of acetic acid with 50 ml of 37% aqueous formalin solution. The mixture is heated at reflux for 48 h, cooled and the solvents evaporated. The residue is triturated with ether and filtered. The filtrate is concentrated and partitioned between ethyl acetate (100 mL) and 5% aqueous acetic acid (100 mL). The aqueous layer is extracted with ethyl acetate (100 mL). The combined organic extracts are washed with 1N NaOH solution, brine, dried over Na2SO4, and concentrated. The crude product is triturated with ethyl acetate to give the product as a white solid, 1H NMR (CDCl3) 7.73 (d, J=5 Hz, 2H), 7.62 (d, J=4 Hz, 2H), 7.3-7.5 (m, 6H), 4.82 (s, 2H), 4.10 (t, J=7 Hz, 2H), 1.7 (m, 2H), 1.25 (m, 2H), 0.8 (t, J=7 Hz, 3H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 48 h
  3. temperaturecooled
  4. customthe solvents evaporated
  5. customThe residue is triturated with ether
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. custompartitioned between ethyl acetate (100 mL) and 5% aqueous acetic acid (100 mL)
  9. extractionThe aqueous layer is extracted with ethyl acetate (100 mL)
  10. washThe combined organic extracts are washed with 1N NaOH solution, brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated
  13. customThe crude product is triturated with ethyl acetate

Sources & evidence

ORD record
ord-15e581a7e0f3411c8af7338b64759367
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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