Imidazole → HCID 54427599, compound

HRID 905075Notes

Reaction equation

HRID 905075 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[O:14][C@@H:13]([O:15][CH:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[CH2:17]Br)[CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[I-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[O:14][C@@H:13]([O:15][CH:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[CH2:17][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)[CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5238Sodium IodideHCID 54124894trans-6-(4-Chlorobenzyloxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran

Product 1

HCID 54427599HCID 54427599, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 121 mg of trans-6-(4-chlorobenzyloxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran, 73 mg of imidazole and 81 mg of sodium iodide in 3 ml of dimethylformamide was heated, with stirring, at 130°-140° C. for 6 hours, after which the mixture was treated and the product purified essentially as described in Example 34(b)(i), to give 66 mg of the title compound, in the form of a colourless oil.

Workup

  1. additionafter which the mixture was treated
  2. customthe product purified essentially

Sources & evidence

ORD record
ord-b2cd88c4360847bda2f743f1984eb5aa
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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