2-Chlorobenzoic Acid → 2-{4-[4-(3,4-Dichlorophenyl)butyl]phenylamino}benzoic acid

HRID 488506Notes

Reaction equation

HRID 488506 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu].[Cu]Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23]([OH:25])=[O:24])=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 136560814-[4-(3,4-Dichlorophenyl)butyl]phenylamine

Product 1

HCID 98664532-{4-[4-(3,4-Dichlorophenyl)butyl]phenylamino}benzoic acid

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound, mp 98-105° C., was prepared from 4-[4-(3,4-dichlorophenyl)butyl]phenylamine (0.50 g, 1.7 mmol), 2-chlorobenzoic acid (0.24 g, 1.56 mmol), anhydrous potassium carbonate (0.71 g, 5.15 mmol), copper powder (0.21 g, 3.28 mmol), and copper(I) chloride (0.015 g, 0.15 mmol) in dry DMF (5 mL) using the procedure described in Example 1, Step C, Method B.

Sources & evidence

ORD record
ord-c7238bc1bb924fc29a8d4a27c5bdfef6
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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