Water → HCID 178489961, compound

HRID 620826Notes

Reaction equation

HRID 620826 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]([CH3:20])=[CH:16][C:15]=1[O:21][CH3:22].P(Cl)(Cl)Cl.O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:22][O:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[C:3]1[NH:2][C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH3:13])[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 100858711-Hydroxy-2-(2-methoxy-4-methylphenyl)-4-methyl-5-(3-pyridyl)imidazole

Product 1

HCID 178489961HCID 178489961, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxy-2-(2-methoxy-4-methylphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.40 g) in N,N-dimethylformamide (28 ml), was added phosphorus trichloride (0.83 ml), and the mixture was stirred for 2 hours at ambient temperature. Then, the solution was poured into water (150 ml), and stirred for an hour at ambient temperature. After neutrallized with aqueous sodium bicarbonate, resulting precipitates were collected by filtration. The precipitates were dried, dissolved in chloroform, and chromatographed on silica gel eluting with a mixture of chloroform and methanol. The fractions were collected, evaporated and triturated in diisopropyl ether to give 2-(2-methoxy-4-methylphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.82 g)

Workup

  1. stirringstirred for an hour at ambient temperature
  2. customresulting
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. customThe precipitates were dried
  6. dissolutiondissolved in chloroform
  7. customchromatographed on silica gel eluting with a mixture of chloroform and methanol
  8. customThe fractions were collected
  9. customevaporated
  10. customtriturated in diisopropyl ether

Sources & evidence

ORD record
ord-fea94de4fd114f25872f76e505de23f5
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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