N,N-Dimethylaniline → 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

HRID 1354256Notes

Reaction equation

HRID 1354256 reaction equation
CN(C)C1C=CC=CC=1.[NH2:10][C:11]1[C:12]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[N:13][C:14]([CH3:23])=[CH:15][C:16]=1[O:17][CH2:18][C:19]([F:22])([F:21])[F:20].[Br:30][CH2:31][C:32](Br)=[O:33]>ClCCl.O>[Br:30][CH2:31][C:32]([NH:10][C:11]1[C:12]([O:24][CH2:25][C:26]([F:29])([F:27])[F:28])=[N:13][C:14]([CH3:23])=[CH:15][C:16]=1[O:17][CH2:18][C:19]([F:21])([F:22])[F:20])=[O:33]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 230924336-Methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-amine

Product 1

HCID 115899302-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N,N-Dimethylaniline (20.46 g, 168.8 mmol) was added to a solution of 3-amino-2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridine (42.29 g, 139.0 mmol) in dichloromethane (600 mL). While the mixture was stirred under cooling with ice, a solution of bromoacetyl bromide (28.73 g, 142.3 mmol) in dichloromethane (100 mL) was added thereto, followed by stirring for ten minutes. The reaction mixture was diluted with water and then extracted with chloroform. The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The thus-obtained crystals were recrystallized from chloroform-hexane, to thereby yield 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide (50.25 g, yield 85%) as colorless needles.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring for ten minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe thus-obtained crystals were recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-f52ff6db4e1e4bddbb770aab5a651433
Source dataset
uspto-grants-2007_05
Patent number
US07223764B2

Reaction notes

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