Acetic Acid → HCID 67900321, compound

HRID 2051577Notes

Reaction equation

HRID 2051577 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][C:31]=1[CH3:40])=[O:29].[C:41]([OH:44])(=[O:43])[CH3:42].C1C[O:48]CC1>O>[C:28]([OH:48])(=[O:29])/[CH:30]=[CH:42]\[C:41]([OH:44])=[O:43].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:26][CH2:27][C:28]([C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1[CH3:40])=[O:29]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14987278HCID 14987278, compound

Product 1

HCID 67900321HCID 67900321, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (E)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-(2-methyl-1-naphthalenyl)-2-propen-1-one (1.25 g), acetic acid (10 ml, THF (10 ml) and water (10 ml) was heated on a steam bath for 1 h. The mixture was then hydrogenated according to the General Procedure and the resulting filtrate was evaporated in vacuo and partitioned between dichloromethane (3×75 ml) and 0.2N sodium hydroxide (100 ml). The combined organic layers were dried and evaporated in vacuo to leave a foam (1.3 g) which was purified by FCC eluting with System A (94.5:5:0.5) to give the free base of the title compound as an oil. The product of maleic acid formation was triturated with ether to give the title compound (0.78 g), m.p. 108°-109°.

Workup

  1. temperaturewas heated on a steam bath for 1 h
  2. customthe resulting filtrate was evaporated in vacuo
  3. custompartitioned between dichloromethane (3×75 ml) and 0.2N sodium hydroxide (100 ml)
  4. customThe combined organic layers were dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-57290324845f48669a668df509be349d
Source dataset
uspto-grants-1991_05
Patent number
US05019586

Reaction notes

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