Benzoyl chloride → 4-(4-Chlorobenzoyl) 3,5-dichlorotoluene

HRID 865082Notes

Reaction equation

HRID 865082 reaction equation
NC1N([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=NC=1C(N)=O.ClC1C=C(C)C=C(Cl)C=1C(O)=O.C(Cl)(=O)C1C=CC=CC=1.S(Cl)(Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3]>CN(C)C=O.ClC1C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([C:11]2[C:12]([Cl:14])=[CH:13][C:8]([CH3:7])=[CH:9][C:10]=2[Cl:24])=[O:23])=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 7412Benzoyl chloride2×HCID 24386Thionyl ChlorideHCID 108144CarboxyamidotriazoleHCID 6451240Aluminum(III) ChlorideHCID 136496822,6-Dichloro-4-methylbenzoic acid

Product 1

HCID 136496514-(4-Chlorobenzoyl) 3,5-dichlorotoluene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7964ChlorobenzeneSolvent

Procedure

The compounds used in the present inventive method are either commercially available or may be prepared using conventional synthetic techniques. Compound 1 can be prepared by the method described in U.S. Pat. No. 4,590,201. Briefly, 2,6-dichloro-4-methylbenzoic acid is converted to its corresponding benzoyl chloride using thionyl chloride in dimethylformamide. Reaction of this benzoyl chloride with chlorobenzene in the presence of aluminum trichloride provides 4-(4-chlorobenzoyl)-3,5-dichlorotoluene. Bromination of the methyl group is carried out using N-bromosuccinimide in the presence of catalytic amounts of dibenzoyl peroxide to provide 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl bromide. The benzyl bromide is then converted to the corresponding benzyl azide using potassium azide. Treatment of the 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl azide thus formed with 2-cyanoacetamide in the presence of sodium methoxide provides after workup, 5-amino-1-(4-(4-chlorobenzoyl)-3,5-dichlorobenzyl)- 1,2,3-triazole-4-carboxamide (Compound 1 ).

Workup

  1. custommay be prepared

Sources & evidence

ORD record
ord-d6df02a897584dfeaf0c6ec1a2c7a770
Source dataset
uspto-grants-1996_10
Patent number
US05565478

Reaction notes

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