4,4'-Dichlorobenzhydryl chloride → 1-[bis(4-chlorophenyl)methyl]-1H-1,2,3-triazole

HRID 2292088

Reaction equation

HRID 2292088 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([CH:13](Cl)[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1>CN(C)C=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[CH:22][CH:23]=1.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 130784,4'-Dichlorobenzhydryl chlorideHCID 24758Sodium hydrideHCID 178418936HCID 178418936, compound

Product 2

HCID 143906541-[bis(4-chlorophenyl)methyl]-1H-1,2,3-triazoleHCID 200349022-[bis(4-chlorophenyl)methyl]-2H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Following the general procedure of Example 1B, 5.0 g of 1,2,3-triazole in 100 ml of dimethylformamide were treated first with 1.44 g of sodium hydride (60% in mineral oil), and then with 5.0 g of 4,4'-dichlorobenzhydryl chloride. The reactants were stirred overnight at about 25° C. and then heated for 1 hour on a steam bath. Chromatography of the residue after work-up provided 2.4 g of the undesired 2-[bis(4-chlorophenyl)methyl]-2H-1,2,3-triazole and 3.1 g of the desired title product, m.p. 124°-125° C.

Workup

  1. temperatureheated for 1 hour on a steam bath

Sources & evidence

ORD record
ord-caf8850777e74c8bbf57ecbeb66f61dd
Source dataset
uspto-grants-1989_01
Patent number
US04801594

Linked notes

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