Triethylamine → N-(1,1-Dimethylpropyl)-2,4-difluorobenzamide

HRID 586797Notes

Reaction equation

HRID 586797 reaction equation
[C:1]([NH2:6])([CH2:4][CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:14][C:15]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:2][C:1]([NH:6][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:15]=1[F:14])([CH3:3])[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 689862-Butanamine, 2-methyl-HCID 516892Sodium BicarbonateHCID 5880812,4-Difluorobenzoyl chloride

Product 1

HCID 9859382N-(1,1-Dimethylpropyl)-2,4-difluorobenzamideYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of t-amylamine (0.35 ml, 3.0 mmol) and triethylamine (0.56 ml, 4.0 mmol) in methylene chloride (3 ml) was added a solution of 2,4-difluorobenzoyl chloride (0.36 g, 2.0 mmol) in methylene chloride (2 ml) with cooling in an ice-bath, and stirred for 1 hour. The reaction mixture was poured over saturated aqueous NaHCO3 and extracted with ethyl acetate. The extract was washed with saturated aqueous NaHCO3 and dried over MgSO4. The solvent was evaporated to give the title compound (0.47 g; >99%).

Workup

  1. temperaturewith cooling in an ice-bath
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0d205412e9a941b782153754c95e2090
Source dataset
uspto-grants-2005_08
Patent number
US06936736B2

Reaction notes

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