Ethanol → 1[4-(4-Chlorobenzoyl)-3,5-dichlorobenzyl]-1,2,3-triazole-4-carboxamide hydrochloride

HRID 580311Notes

Reaction equation

HRID 580311 reaction equation
N[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[C:12]([Cl:14])[C:11]([C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:10]([Cl:24])[CH:9]=2)[N:5]=[N:4][C:3]=1[C:25]([NH2:27])=[O:26].Cl.C(=N)(OCC)C.C(O)C>C(OCC)C>[ClH:14].[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:11]2[C:12]([Cl:14])=[CH:13][C:8]([CH2:7][N:6]3[CH:2]=[C:3]([C:25]([NH2:27])=[O:26])[N:4]=[N:5]3)=[CH:9][C:10]=2[Cl:24])=[O:23])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 108144CarboxyamidotriazoleHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 867422361[4-(4-Chlorobenzoyl)-3,5-dichlorobenzyl]-1,2,3-triazole-4-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-amino-1-[4-(4-chlorobenzoyl)-3,5-dichlorobenzyl]-1,2,3-triazole-4-carboxamide (4.3 g), ethyl acetimidate hydrochloride (1.2 g) and absolute ethanol (50 ml) is heated at reflux under nitrogen for 20 hours. The reaction mixture is cooled and diluted with ethyl ether (50 ml). The solid is filtered and dried to give 5-((amino)ethylidine) amino)-1[4-(4-chlorobenzoyl)-3,5-dichlorobenzyl]-1,2,3-triazole-4-carboxamide hydrochloride.

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 20 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationThe solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-4f04dcb691884d1f87251948a579b770
Source dataset
uspto-grants-1988_06
Patent number
US04752611

Reaction notes

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