Phosphorus oxychloride → 2-Chloro-5-[3-(1-imidazolyl)propyl]pyridine

HRID 322318Notes

Reaction equation

HRID 322318 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12](OC)=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.P(Cl)(Cl)([Cl:19])=O.C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:19][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 220098285-[3-(1-Imidazolyl)propyl]-2-methoxypyridine

Product 1

HCID 220095902-Chloro-5-[3-(1-imidazolyl)propyl]pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-[3-(1-imidazolyl)propyl]-2-methoxypyridine(2.10 g), phosphorus oxychloride (7.44 g) and N,N-dimethylformamide (14.6 g) was stirred at 100° C. for 10 hours. To the reaction mixture was added saturated aqueous sodium acetate and saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel chloromatography. From the fraction eluted with ethyl acetate-methanol (20:1, v/v), 2-chloro-5-[3-(1-imidazolyl)propyl]pyridine (1.28 g, 60%) was obtained. Oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washFrom the fraction eluted with ethyl acetate-methanol (20:1

Sources & evidence

ORD record
ord-6a2b6e329e314a9c91887818ff7f1c55
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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