4-Bromoaniline → N-(4-bromophenyl)-3-(3-chlorophenyl)propanamide

HRID 928737Notes

Reaction equation

HRID 928737 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][C:25](O)=[O:26])[CH:20]=[CH:21][CH:22]=1.CCN=C=NCCCN(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:25](=[O:26])[CH2:24][CH2:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1771643-(3-Chlorophenyl)propanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 1407353N-(4-bromophenyl)-3-(3-chlorophenyl)propanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (1.01 mL, 7.27 mmol) was added slowly to a mixture of 4-bromoaniline (0.500 g, 2.91 mmol), 3-(3-chlorophenyl)propanoic acid (0.643 g, 2.91 mmol), and EDCI (0.669 g, 3.49 mmol) in CH2Cl2 (20 mL). The mixture was stirred at room temperature for 48 hours and saturated aqueous NaHCO3 was added. Water (50 mL) was added followed by additional CH2Cl2. The mixture as stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4, then filtered. The solvent was removed under reduced pressure and the residual oil chromatographed (CH2Cl2/EtOAc) to provide the title compound as a white fluffy solid.

Workup

  1. stirringThe mixture as stirred for 10 minutes
  2. customlayers were separated
  3. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residual oil chromatographed (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-b4fdfe9ea8fa4d4f871665aa31bd806d
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

Loading…