Water → 2-(2-Methoxyphenyl)-5-methyl-4-(3-pyridyl)imidazole

HRID 620824Notes

Reaction equation

HRID 620824 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][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].P(Cl)(Cl)Cl.O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][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 99938631-Hydroxy-2-(2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

Product 1

HCID 100157112-(2-Methoxyphenyl)-5-methyl-4-(3-pyridyl)imidazoleYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxy-2-(2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.5 g) in N,N-dimethylformamide (10 ml) was added phosphorus trichloride (0.31 ml) under ice-cooling. The mixture was stirred for 2 hours at 5° to 10° C. The mixture was poured into water (100 ml), and neutralized with aqueous sodium bicarbonate. The precipitate was collected, washed with water, and dried to give 2-(2-methoxyphenyl)-5-methyl-4-(3-pyridyl)imidazole (0.31 g).

Workup

  1. temperaturecooling
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6d5627bd0ba6441195e040fc9e5b1df7
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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