Tert-Butylamine → N-tert-butyl-4-(trifluoromethyl)benzamide

HRID 650109Notes

Reaction equation

HRID 650109 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[F:6][C:7]([F:18])([F:17])[C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1>C1C=CC=CC=1.ClCCl>[C:1]([NH:5][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([C:7]([F:6])([F:17])[F:18])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 676074-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 9881334N-tert-butyl-4-(trifluoromethyl)benzamideYield 429%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To N-tert-butylamine (3.50 g, 0.0048 mol) in 75 mL of benzene was added 4-trifluoromethylbenzoyl chloride (5.00 g, 0.024 mol). The temperature was maintained below 15° C. during the addition and then the reaction mixture was allowed to warm to ambient temperature and stirred for 3 hours. The solvent was then stripped and the residue was dissolved in 75 mL of dichloromethane. This solution was washed with 5% hydrochloride acid (2×75 mL), water (2×75 mL), dried over MgSO4 and then the solvent was removed in vacuo to provide 5.05 g (85-9% yield) of the title compound, m.p. 146-148° C.

Workup

  1. temperatureThe temperature was maintained below 15° C. during the addition
  2. washThis solution was washed with 5% hydrochloride acid (2×75 mL), water (2×75 mL)
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a821887250b94f9faf1d3301b6e38321
Source dataset
uspto-grants-2001_08
Patent number
US06271265B1

Reaction notes

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