Water → N-[2-(3-bromo-phenyl)-ethyl]-2-chloro-benzamide

HRID 1713085Notes

Reaction equation

HRID 1713085 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][NH2:7].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:6][NH:7][C:14](=[O:15])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[Cl:11])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 691102-Chlorobenzoyl chlorideHCID 70217363-Bromophenethylamine

Product 1

HCID 57420566N-[2-(3-bromo-phenyl)-ethyl]-2-chloro-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromophenethylamine (10.0 g, 50 mmol) in DCM (100 ml) containing TEA (8.36 g, 60 mmol, 1.2 eq.) cooled to 0° C. is added 2-chlorobenzoylchloride (8.75 g, 50 mmol, 1.0 eq.) portionwise. The resulting mixture is stirred at rt for 1 hr. Water (100 ml) is added to quench the reaction. The organic layer is collected, washed with water and brine, dried over sodium sulfate, and concentrated to give the title compound.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer is collected
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15da251e30bb4308b85a510124c4aed7
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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