Imidazole → 2-(4-Chlorophenyl)-2-(1H-imidazol-1-ylmethyl)-4-[4-(4-acetylpiperazin-1-ylmethyl)-2-chloro-6-methylphenoxymethyl]-1,3-dioxolane

HRID 1074428Notes

Reaction equation

HRID 1074428 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([Cl:19])[CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].CS(O[CH2:27][CH:28]1[CH2:32][O:31][C:30]([CH2:40]Br)([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[O:29]1)(=O)=O.[I-].[K+].[Na].[NH:45]1[CH:49]=[CH:48][N:47]=[CH:46]1>CC(N(C)C)=O>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([C:30]2([CH2:40][N:45]3[CH:49]=[CH:48][N:47]=[CH:46]3)[O:29][CH:28]([CH2:27][O:18][C:14]3[C:15]([CH3:17])=[CH:16][C:11]([CH2:10][N:7]4[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]4)=[CH:12][C:13]=3[Cl:19])[CH2:32][O:31]2)=[CH:38][CH:37]=1

Participants

8

Reactant 6

HCID 795ImidazoleHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 5360545SodiumHCID 155764424-(4-Acetylpiperazin-1-ylmethyl)-2-chloro-6-methylphenolHCID 155764512-Bromomethyl-2-(4-chlorophenyl)-1,3-dioxolan-4-ylmethyl methanesulfonate

Product 1

HCID 204965612-(4-Chlorophenyl)-2-(1H-imidazol-1-ylmethyl)-4-[4-(4-acetylpiperazin-1-ylmethyl)-2-chloro-6-methylphenoxymethyl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2.8 g=10 mmoles of 4-(4-acetylpiperazin-1-ylmethyl)-2-chloro-6-methylphenol are added in portions, while cooling and stirring, to a suspension of 0.3 g=10 mmoles of sodium hydride (an 80% strength dispersion in oil) in 20 ml of dimethylacetamide at such a rate that the temperature does not exceed 20° C. 4.1 g=10 mmoles of 2-bromomethyl-2-(4-chlorophenyl)-1,3-dioxolan-4-ylmethyl methanesulfonate are then introduced in portions and stirring is continued for 6 hours at 80° C. 0.8 g=5 mmoles of potassium iodide and 0.9 g=10 mmoles of the sodium salt of imidazole are introduced at this temperature and the mixture is then stirred for 48 hours at 160° C. and worked up as described in Example 1a. This gives 2 g (35% of theory) of a highly viscous, non-crystalline oil.

Workup

  1. temperaturewhile cooling
  2. customdoes not exceed 20° C
  3. stirringthe mixture is then stirred for 48 hours at 160° C.

Sources & evidence

ORD record
ord-7f4c17c2e1c0490d9fb9b7860df783f7
Source dataset
uspto-grants-1983_07
Patent number
US04391805

Reaction notes

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