Acetic Acid → HCID 67900102, compound

HRID 2073522Notes

Reaction equation

HRID 2073522 reaction equation
[CH3:1][C:2]1[N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=[N:4][C:3]=1/[CH:26]=[CH:27]/[C:28]([C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)=[O:29].C1C[O:43]CC1.[C:45]([OH:48])(=[O:47])[CH3:46]>O>[C:28]([OH:43])(=[O:29])/[CH:30]=[CH:46]\[C:45]([OH:48])=[O:47].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1/[CH:26]=[CH:27]/[C:28]([C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)=[O:29]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14987242HCID 14987242, compound

Product 1

HCID 67900102HCID 67900102, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (E)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-(1-naphthalenyl)-2-propen-1-one (1.0 g) in a mixture of water (10 ml), THF (10 ml) and acetic acid (10 ml) was heated at reflux under nitrogen for 1 h. The cooled reaction mixture was partitioned between ethyl acetate (100 ml; discarded) and 0.4N hydrochloric acid (2×75 ml). The combined acidic layers were basified with potassium carbonate (to pH8) and extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried and evaporated in vacuo to give the free base of the title compound (0.51 g) as a solid. This was dissolved in hot methanol (15 ml), and a solution of maleic acid (0.23 g) in methanol (2 ml) was added with stirring. Cooling precipitated the title compound (0.62 g), m.p. 170°-173° (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 1 h
  3. customThe cooled reaction mixture
  4. customwas partitioned between ethyl acetate (100 ml; discarded) and 0.4N hydrochloric acid (2×75 ml)
  5. extractionextracted with dichloromethane (3×50 ml)
  6. dry with materialThe combined dichloromethane extracts were dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0b1e7b9fdbee4f42a4a649106b9be985
Source dataset
uspto-grants-1990_04
Patent number
US04918080

Reaction notes

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