Water → HCID 178437573, compound

HRID 620828Notes

Reaction equation

HRID 620828 reaction equation
O[N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH2:13][CH3:14])[N:4]=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1.P(Cl)(Cl)Cl.O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([C:3]2[NH:2][C:6]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)=[C:5]([CH2:13][CH3:14])[N:4]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 14211324HCID 14211324, compound

Product 1

HCID 178437573HCID 178437573, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxy-2-(3,4-dimethoxyphenyl)-4-ethyl-5-(3-pyridyl)imidazole (1.86 g) in N,N-dimethylformamide (38 ml) was added phosphorus trichloride (0.10 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 1% to 5%). The fractions were collected and evaporated to give 2-(3,4-dimethoxyphenyl)-4-ethyl-5-(3-pyridyl)imidazole (0.89 g), which was diluted with methanol (8 ml). 1.2 Equivalent of hydrogen chloride gas was bubbled thereinto and diethyl ether was added to the mixture under cooling. The precipitate was collected and dried to give 2-(3,4-dimethoxyphenyl)-4-ethyl-5-(3-pyridyl)imidazole hydrochloride (0.43 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 1% to 5%)
  7. customThe fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-17c078b4893a43c8891a25a0a5384e56
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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