2-Chlorobenzoic Acid → 2-{4-[2-(4-Dibutylamino-phenyl)-ethyl]phenylamino}-benzoic acid

HRID 488492Notes

Reaction equation

HRID 488492 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N[C:16]1([NH:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)=[CH:18][CH2:17]1)CCC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu].[Cu]Cl>[CH2:10]([N:31]([CH2:32][CH2:33][CH2:34][CH3:35])[C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:2]3[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])=[CH:28][CH:29]=2)=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 86594891HCID 86594891, compound

Product 1

HCID 222696822-{4-[2-(4-Dibutylamino-phenyl)-ethyl]phenylamino}-benzoic acidYield 18.6%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 2-chlorobenzoic acid (1.46 g, 9.36 mmol), 4-[2-(4,4-dibutylaminophenyl)ethyl]phenylamine (3.31 g, 10.20 mmol), anhydrous potassium carbonate (4.27 g, 30.88 mmol), copper powder (1.25 g, 19.65 mmol), and copper(I) chloride (0.092 g, 0.93 mmol) in dry DMF (30 mL) using the procedure described in Example 1, Step C, Method B. This procedure yielded a 0.39 g (0.87 mmol, 8.6%) of the desired product. mp 115-117° C.

Sources & evidence

ORD record
ord-e0761f2215a5472dac2c64bded80ab9e
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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