Imidazole → (2,4-Dichlorobenzyl)-{4-[2-(1-imidazolyl)-ethyl]-phenyl}-ether, Hydrochloride

HRID 435886Notes

Reaction equation

HRID 435886 reaction equation
[Cl:1]C1C=C(Cl)C=CC=1COC1C=CC(CCO)=CC=1.S(Cl)(Cl)=O.Cl[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=2[Cl:42])=[CH:29][CH:28]=1.[NH:43]1[CH:47]=[CH:46][N:45]=[CH:44]1.[Na].N1C=CN=C1.[H-].[Na+]>CN(C)C=O>[ClH:1].[Cl:42][C:36]1[CH:37]=[C:38]([Cl:41])[CH:39]=[CH:40][C:35]=1[CH2:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH2:25][N:43]2[CH:47]=[CH:46][N:45]=[CH:44]2)=[CH:28][CH:29]=1

Participants

8

Reactant 6

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 125273774-(2,4-Dichlorobenzyloxy)-phenethyl alcoholHCID 214816562,4-Dichloro-1-{[4-(2-chloroethyl)phenoxy]methyl}benzeneHCID 57373095Imidazole sodium

Product 1

HCID 131710637(2,4-Dichlorobenzyl)-{4-[2-(1-imidazolyl)-ethyl]-phenyl}-ether, Hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.8 g. of sodium hydroxide in 10 ml. of water and 13.6 g. of 2,4-dichlorobenzyl alcohol are added to 8 g. of 4-hydroxyphenethyl alcohol in 80 ml. of ethanol. After refluxing the solution for 1.5 hours, the mixture is acidified with dilute sulfuric acid and extracted with methylene chloride. Drying and evaporation of the solvent yields the crude product at 100°-130° (air bath temperature)//0.02 torr by distillation with the use of a bulb tube. From cyclohexane, 14.5 g. of 4-(2,4-dichlorobenzyloxy)-phenethyl alcohol is obtained, m.p. 55°. The alcohol is converted, by 10 minutes of heating with thionyl chloride, into the [4-(β-chloroethyl)-phenyl]-(2,4-dichlorobenzyl)-ether and added to a solution of sodium imidazole, obtained by reacting 2 g. of imidazole with 1.04 g. of 80% strength sodium hydride - oil suspension in 30 ml. of dimethylformamide; the mixture is agitated for 6 hours at 100°-120° . The product is worked up as indicated in Example 56.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-61c70f35c1aa459ca140be0b2768d436
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Reaction notes

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