1-Chloro-4-(chloromethyl)benzene → Ethyl 4-[1-(4-chlorobenzyl)benzimidazol-2-yl]-3,3-dimethylbutanoate

HRID 1493326Notes

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][C:11]([CH3:19])([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>CN(C)C=O>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[CH2:10][C:11]([CH3:18])([CH3:19])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 50 °C

Procedure

9 g of ethyl 4-(benzimidazol-2-yl)-3,3-dimethylbutanoate, prepared in Example 40, are added to a suspension of 21.5 g of 60% sodium hydride in 50 ml of anhydrous dimethylformamide. The mixture is stirred for 1 hour at 50° C., 5.6 g of 4-chlorobenzyl chloride are then added and the solution obtained is heated for 5 hours at 90° C. The solvents are concentrated under vacuum and the residue is taken up with water and then extracted with ether. The ether phase is washed with water and then dried over magnesium sulfate and the ether is evaporated off to dryness to give 12.9 g of ethyl 4-[1-(4-chlorobenzyl)benzimidazol-2-yl]-3,3-dimethylbutanoate in the form of an oil, which is used as such for the next step.

Workup

customthe solution obtained
temperatureis heated for 5 hours at 90° C
concentrationThe solvents are concentrated under vacuum
extractionextracted with ether
washThe ether phase is washed with water
dry with materialdried over magnesium sulfate
customthe ether is evaporated off to dryness

Sources & evidence

ORD record: ord-27dee4e70fc24f47a03ce5671d887828
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021443

Reaction notes

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