Hydrochloric Acid → 1-(2,4-Dichlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole

HRID 984792Notes

Reaction equation

HRID 984792 reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])(=O)[CH3:2].Cl>C(O)C>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[CH2:17][N:16]1[C:6]2[CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:14]=[CH:15][C:5]=2[N:4]=[C:1]1[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22508831Ethyl 4-(acetylamino)-3-((2,4-dichlorobenzyl)amino)benzoate

Product 1

HCID 225087251-(2,4-Dichlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 250 g of ethyl 4-(acetylamino)-3-((2,4-dichlorobenzyl)amino)benzoate, 68.4 g of concentrated hydrochloric acid, and 1197 g of ethanol was refluxed for 2 hours, to give 1-(2,4-dichlorobenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole. To this reaction solution, a solution consisting of 105 g of sodium hydroxide and 1000 g of water was added, and the reaction solution was refluxed for 2 hours. The reaction solution was cooled, and was neutralized with the slow addition of 193.3 g of concentrated hydrochloric acid. The crystals precipitated were separated through filtration, were washed with 900 ml of a mixed solution of ethanol and water at a ratio of 2:1, and were dried to give 214 g of the title compound.

Workup

  1. temperaturewas refluxed for 2 hours

Sources & evidence

ORD record
ord-5d4528a75d234478a63d3913668653b3
Source dataset
uspto-grants-2005_03
Patent number
US06869950B1

Reaction notes

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