Triethylamine → N-(4-fluorophenyl)-2,2-dimethylpropanamide

HRID 369735Notes

Reaction equation

HRID 369735 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>C(Cl)Cl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 62493Pivaloyl chloride

Product 1

HCID 310095N-(4-fluorophenyl)-2,2-dimethylpropanamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 125 mL of 4-fluoroaniline and 18.4 mL of triethylamine in 300 mL of methylene chloride was added dropwise over 30 min 14.8 mL of trimethylacetyl chloride. After addition was complete, the cooling bath was removed and stirring was continued at ambient temperature for 1 h. The reaction mixture was brought to pH 3 with 6N HCl and was partitioned between methylene chloride and water. Evaporation of the organiclayer afforded a solid which was collected and washed with hexane to afford 21.35 g (83%) of the title compound as a crystalline solid.

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. customwas partitioned between methylene chloride and water
  4. customEvaporation of the
  5. customorganiclayer afforded a solid which
  6. customwas collected
  7. washwashed with hexane

Sources & evidence

ORD record
ord-667e17b7e71a4644a58d599337033ff5
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

Loading…