Ammonia → 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionamide

HRID 45495Notes

Reaction equation

HRID 45495 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:22]1C=CN=C1)=O.N>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10]([NH2:22])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 576913963-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid

Product 1

HCID 576913943-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionamideYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid* (0.25 g, 0.74 mmol) and 1,1′-carbonyldiimidazole (0.249, 1.47 mmol) in dichloromethane was stirred for 45 minutes before the addition of ammonia (2M solution in methanol, 3.68 ml, 7.36 mmol). The reaction mixture was stirred for 2 hours, solvent removed under reduced pressure and residue was purified over flash silica chromatography eluting with ethyl acetate/petroleum ether (1:4) to afford the title compound (0.091 g, 36% yield). LC/MS: (PS-A2) Rt 3.08 [M+H]+ 339.93.

Workup

  1. customsolvent removed under reduced pressure and residue
  2. customwas purified over flash silica chromatography
  3. washeluting with ethyl acetate/petroleum ether (1:4)

Sources & evidence

ORD record
ord-f0d8fb3a326849fba3da29817735ab46
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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