Acetyl chloride → N-[7-(Trifluoromethyl)-2-naphthalenyl]acetamide

HRID 1270757Notes

Reaction equation

HRID 1270757 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH2:13])=[CH:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH:13][C:23](=[O:25])[CH3:24])=[CH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 184515397-(Trifluoromethyl)naphthalen-2-amine

Product 1

HCID 18451538N-[7-(Trifluoromethyl)-2-naphthalenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-trifluoromethyl-2-aminonaphthalene (550 mg, 2.60 mmol) and triethylamine (1.09 mL, 7.81 mmol) in dichloromethane (10 mL) at room temperature is added acetyl chloride (0.222 mL, 3.13 mmol) dropwise. After stirring at room temperature for 1.5 hours, the mixture is partitioned between dichloromethane and water. The organic layer is washed with 0.1 M citric acid solution, brine, dried (MgSO4) and concentrated by rotary evaporator to give 7-trifluoromethyl-2-acetamidonaphthalene as a light yellow solid.

Workup

  1. customthe mixture is partitioned between dichloromethane and water
  2. washThe organic layer is washed with 0.1 M citric acid solution, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-d8eb814c16ab403ca891abc81650745b
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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