Triethylamine → 2-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide

HRID 1253827Notes

Reaction equation

HRID 1253827 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.C(N(CC)CC)C.[Br:18][CH:19]([CH3:23])[C:20](Br)=[O:21].C(=O)([O-])O.[Na+]>O1CCCC1>[Br:18][CH:19]([CH3:23])[C:20]([NH:6][C:5]1[C:7]([CH3:9])=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 905494-Bromo-2,6-xylidineHCID 516892Sodium Bicarbonate

Product 1

HCID 600353552-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2,6-dimethylaniline (100.0 g) in tetrahydrofuran (400 mL) was added triethylamine (60.7 g) and 2-bromopropionyl bromide (129.5 g) under ice-cooling. The mixture was stirred at room temperature for 1 hour and cooled in an ice-cooling bath. To the reaction mixture was added a sodium hydrogencarbonate aqueous solution and the mixture was stirred at room temperature for 30 minutes. The precipitate was collected by filtration, washed with water and diethyl ether, and dried to give 2-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide (151.2 g).

Workup

  1. temperaturecooling
  2. temperaturecooling bath
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-21ed26b6a8294e968cfc271412bfa216
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

Loading…