Water → HCID 10017395, compound

HRID 620825Notes

Reaction equation

HRID 620825 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])=[CH:16][C:15]=1[O:22][CH3:23].P(Cl)(Cl)Cl.O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[C:3]1[NH:4][C:5]([CH3:13])=[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 9972731HCID 9972731, compound

Product 1

HCID 10017395HCID 10017395, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxy-2-(2,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (6.6 g) in N,N-dimethylformamide (130 ml) was added phosphorus trichloride (3.7 ml) under ice-cooling. The mixture was stirred for 2 hours at 5° to 10° C. The reaction mixture was poured into water, neutralized with aqueous sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue was subjected to column chromatography on silica gel eluting with a mixture of chloroform and methanol (methanol 0% to 15%). The fractions were collected and evaporated to give 2-(2,4-dimethoxypheyl)-5-methyl-4-(3-pyridyl)imidazole (2.82 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of chloroform and methanol (methanol 0% to 15%)
  7. customThe fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-49003496a9b74b4f8bdb84f1d1f21905
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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