Sodium Carbonate → HCID 178488938, compound

HRID 620823Notes

Reaction equation

HRID 620823 reaction equation
O[N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH3:13])[N:4]=[C:3]1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1.P(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:3]2[NH:2][C:6]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)=[C:5]([CH3:13])[N:4]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24387Phosphorus trichlorideHCID 142113151-Hydroxy-2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

Product 1

HCID 178488938HCID 178488938, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-hydroxy-2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.68 g) in methylene chloride (9 ml) was added phosphorus trichloride (0.76 ml) at ambient temperature. The mixture was refluxed for 1 hour, and cooled. The mixture was adjusted to pH 7.8 with aqueous sodium carbonate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated. The residue was triturated with diisopropyl ether to give 2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.39 g).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-d7a7a69ca50a454ab5e38d10dcdb7a88
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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