Imidazole → HCID 54274426, compound

HRID 905079Notes

Reaction equation

HRID 905079 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:10]=1[O:11][CH2:12][C@@H:13]1[O:18][C@@H:17]([O:19][CH:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:21]Cl)[CH2:16][CH2:15][CH2:14]1.[I-].[Na+]>CN(C)C=O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][CH:20]([O:19][C@H:17]2[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:12][O:11][C:10]3[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:9]=3[Cl:8])[O:18]2)[CH2:21][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 53926027HCID 53926027, compound

Product 1

HCID 54274426HCID 54274426, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 90 mg of imidazole and 58 mg of 55% sodium hydride in 2 ml of dimethylformamide was stirred at 80° C. for 30 minutes and then left to cool to room temperature. 2 ml of a dimethylformamide solution containing 420 mg of trans-6-(2,4-dichlorophenoxymethyl)-2-[1-chloro-4-(4-chlorophenyl)-2-butoxy]tetrahydropyran and 132 mg of sodium iodide were then added to the mixture and stirring was continued at 90° C. for 4 hours. The mixture was then treated and the product purified essentially as described in Example 34(b)(i), to give 193 mg of the title compound as a colourless oil containing approximately B 1:1 mixture of isomers.

Workup

  1. waitleft
  2. additionwere then added to the mixture
  3. additionThe mixture was then treated
  4. customthe product purified essentially

Sources & evidence

ORD record
ord-9d6bcbc9220a459d888e069ecad8a5e0
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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