Hydrochloric Acid → 3-(3,5-Dichloro-phenylamino)-N-phenyl-benzamide

HRID 1387517Notes

Reaction equation

HRID 1387517 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[Cl:17][C:18]1[CH:19]=[C:20](I)[CH:21]=[C:22]([Cl:24])[CH:23]=1.C(N1CCOCC1)C.Cl>CN(C)C=O.C(Cl)(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[Cl:17][C:18]1[CH:19]=[C:20]([NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])[CH:21]=[C:22]([Cl:24])[CH:23]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 764241,3-Dichloro-5-iodobenzeneHCID 843473-Aminobenzanilide

Product 1

HCID 186262113-(3,5-Dichloro-phenylamino)-N-phenyl-benzamideYield 3%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-N-phenyl-benzamide (2.0 g, 9.4 mmol), 3,5-dichloroiodobenzene (2.65 g, 9.7 mmol), N-ethylmorpholine (1.1 g, 9.5 mmol), and copper(II) acetate (0.1 g, 0.6 mmol) in N,N-dimethylformamide (6 mL) was stirred under an inert atmosphere and heated to reflux. After 120 hours, the mixture was allowed to cool and was stirred into water (300 mL) and acidified with concentrated hydrochloric acid. The mixture was extracted with dichloromethane (300 mL) and the extract separated and washed successively with 2N hydrochloric acid, water, 0.5 M aqueous potassium carbonate, water, and saturated aqueous sodium chloride, then dried over MgSO4. The solution was filtered and stripped of solvent under reduced pressure to leave a solid residue which was subjected to chromatography on a column of silica gel in chloroform to afford the product (0.1 g); m.p. 164-165° C. after recrystallization from ethyl alcohol.

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. extractionThe mixture was extracted with dichloromethane (300 mL)
  4. customthe extract separated
  5. washwashed successively with 2N hydrochloric acid, water, 0.5 M aqueous potassium carbonate, water, and saturated aqueous sodium chloride
  6. dry with materialdried over MgSO4
  7. filtrationThe solution was filtered
  8. customto leave a solid residue which

Sources & evidence

ORD record
ord-2110df1b95ab4660964e0c557b42f7fa
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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