Phenylacetic Acid → HCID 10475763, compound

HRID 1033889Notes

Reaction equation

HRID 1033889 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[C:20]1([CH2:26][C:27]([OH:29])=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)(=O)C>O>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7](/[CH:10]=[C:26](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[C:27]([OH:29])=[O:28])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-

Product 1

HCID 10475763HCID 10475763, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde (554 mg, 2 mmol), phenylacetic acid (310 mg, 2.3 mmol), potassium carbonate (126 mg, 0.91 mmol), and acetic anhydride (1 mL) was heated gradually to 140° C. and held at this temperature for 6 hours. The cooled reaction was diluted with water and the oily solid was separated, triturated several times with ether, and the solid was crystallized several times from methanol/ethyl acetate to give 143 mg (18%) of the title compound; mp 210°-212° C. The NMR was consistent with the trans olefinic product.

Workup

  1. customThe cooled reaction
  2. customthe oily solid was separated
  3. customtriturated several times with ether
  4. customthe solid was crystallized several times from methanol/ethyl acetate

Sources & evidence

ORD record
ord-7959a419420e441b8cee5af31ea564df
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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