4-Chloroaniline → 4-Bromo-N-(2,2-dichloro-1-(4-chlorophenylamino)butyl)benzamide

HRID 1920087Notes

Reaction equation

HRID 1920087 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH:9](O)[C:10]([Cl:14])([Cl:13])[CH2:11][CH3:12])=[O:7])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH:9]([NH:29][C:28]2[CH:30]=[CH:31][C:25]([Cl:24])=[CH:26][CH:27]=2)[C:10]([Cl:14])([Cl:13])[CH2:11][CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 24819Phosphorus pentachlorideHCID 581495534-bromo-N-(2,2-dichloro-1-hydroxybutyl)benzamide

Product 1

HCID 581495564-Bromo-N-(2,2-dichloro-1-(4-chlorophenylamino)butyl)benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-bromo-N-(2,2-dichloro-1-hydroxybutyl)benzamide 119 (0.84 g, 2.48 mmol) in chloroform (15 mL) was reacted with PCl5 (0.54 g, 2.46 mmol) at 50° C. for 30 minutes. The mixture was cooled to room temperature and quenched with ice. The aqueous layer was extracted with ether. The organic solution was dried over MgSO4, filtered, and reacted with 4-chloroaniline (0.66 g, 5.17 mmol). The mixture was stirred for 18 hours at room temperature. An acidic, (HCl) aqueous workup and ether extraction preceded chromatographic purification on silica gel (7:3 hexane:CH2Cl2). 4-Bromo-N-(2,2-dichloro-1-(4-chlorophenylamino)butyl)benzamide (Compound-15) was obtained as a white solid (701 mg, 62%). 1H NMR (300 MHz, CDCl3): δ=7.64-7.56 (m, 4H), 7.16 (d, J=9.0 Hz, 2H), 6.73 (d, J=8.7 Hz, 2H), 6.48 (d, J=9.6 Hz, 1H), 6.01 (d, J=9.0 Hz, 1H), 2.50-2.27 (m, 2H), 1.27 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched with ice
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. extractionAn acidic, (HCl) aqueous workup and ether extraction
  6. custompurification on silica gel (7:3 hexane:CH2Cl2)

Sources & evidence

ORD record
ord-40bf829c0dc049168f3a1fa713eda948
Source dataset
uspto-grants-2012_05
Patent number
US08168795B2

Reaction notes

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