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

HRID 924703Notes

Reaction equation

HRID 924703 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 (0.24 g, 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. *This starting material can be made by the method described in Example 8A through to 8C.

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-8834ed7bff504474802432ea0fde3b6e
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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