Water → HCID 70544649, compound

HRID 1759249Notes

Reaction equation

HRID 1759249 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]([CH2:10][C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH2:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.O>CN(C)C=O.C(OCC)C>[CH2:25]([O:24][C:22]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:3][C:4]2[C:5]([CH2:10][C:11]3[NH:15][CH:14]=[CH:13][N:12]=3)=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:28][CH:27]=1)=[O:23])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 70545010HCID 70545010, compound

Product 1

HCID 70544649HCID 70544649, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (1.81 g of 50% dispersion in mineral oil) was added in portions to a stirred solution of 3-hydroxy-2-(1-imidazolylmethyl)pyridine (6.00 g) in dry N,N-dimethylformamide (100 ml) at 0° C. The mixture was stirred for 15 minutes and a solution of ethyl 4-bromomethyl-benzoate (8.34 g) in dry N,N-dimethylformamide (20 ml) was then added over a period of 10 minutes. The mixture was allowed to warm to room temperature, stirred for 4 hours and water (5 ml) was then added. The solution was evaporated and the residue chromatographed on silica gel, eluting with chloroform. The product-containing fractions were combined and evaporated to give an oil which solidified on trituration with diethyl ether. Recrystallization from diethyl ether gave 3-(4-ethoxycarbonylbenzyloxy)-2-(1-imidazolylmethyl)pyridine (4.85 g), m.p. 100°-101° C.

Workup

  1. stirringstirred for 4 hours
  2. customThe solution was evaporated
  3. customthe residue chromatographed on silica gel
  4. washeluting with chloroform
  5. customevaporated
  6. customto give an oil which
  7. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-a41b42966c4f422b88544b910eb4db3b
Source dataset
uspto-grants-1982_07
Patent number
US04339583

Reaction notes

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