Water → N-(2-bromo-5-chloro-phenyl)-3-chloro-benzamide

HRID 1810974Notes

Reaction equation

HRID 1810974 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22].O>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH:4][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][CH:26]=[C:18]([Cl:17])[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 113102762-Bromo-5-chloroaniline

Product 1

HCID 59548898N-(2-bromo-5-chloro-phenyl)-3-chloro-benzamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-chloroaniline (0.380 g, 1.84 mmol) and triethylamine (0.768 mL, 5.52 mmol) in dichloromethane (15 mL) is added 3-chlorobenzoyl chloride (0.353 mL, 2.76 mmol) in a dropwise fashion. The resulting mixture is allowed to stir at room temperature for 2 h. Water (30 mL) is added and extracted with the mixture is extracted with dichloromethane 3×. The organic layer is combined, washed with brine 1×, dried (Na2SO4) and concentrated under vacuum to give 0.630 g of N-(2-bromo-5-chloro-phenyl)-3-chloro-benzamide in 99% yield.

Workup

  1. extractionextracted with the mixture
  2. extractionis extracted with dichloromethane 3×
  3. washwashed with brine 1×
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-235ebf30887f49599a01deb5c35746eb
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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