Triethylamine → HCID 22933624, compound

HRID 1269843Notes

Reaction equation

HRID 1269843 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[C:17]([F:20])([F:19])[F:18].[C:21](Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>ClCCl>[CH3:8][O:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:12][C:11]=1[C:17]([F:18])([F:19])[F:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 6007055-Amino-2-methoxybenzotrifluoride

Product 1

HCID 22933624HCID 22933624, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (6.24 ml, 44.8 mmol) was added to a solution of 4-methoxy-3-(trifluoromethyl)aniline (4.29 g, 22.4 mmol) in dichloromethane (45.0 ml), and the resulting mixture was ice-cooled, followed by adding dropwise thereto pivaloyl chloride (2.84 g, 23.5 mmol) at 0 to 5° C. The resulting mixture was warmed up to room temperature and stirred for 1 hour while maintaining the temperature. The mixture was partitioned by the use of a 5%-aqueous sodium hydrogencarbonate solution and ethyl acetate, and the organic layer was washed with a 5% aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain N-[4-methoxy-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide (6.16 g, 100%).

Workup

  1. temperaturecooled
  2. additionby adding dropwise
  3. customat 0 to 5° C
  4. temperaturewhile maintaining the temperature
  5. customThe mixture was partitioned by the use of a 5%-aqueous sodium hydrogencarbonate solution and ethyl acetate
  6. washthe organic layer was washed with a 5% aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9b80f7477324458ad949268483fd320
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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