Potassium Carbonate → N,N,4-Triethyl-2-(trifluoromethyl)benzamide

HRID 2100607Notes

Reaction equation

Cl[C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[O:7])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([Zn]CC)[CH3:26]>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:9]([N:8]([CH2:11][CH3:12])[C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([CH2:25][CH3:26])=[CH:3][C:4]=1[C:15]([F:18])([F:17])[F:16])[CH3:10]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-chloro-N,N-diethyl-2-(trifluoromethyl)benzamide (5.04 g, 18 mmol) in 100 mL of N,N-dimethylformamide was added potassium carbonate (6.2 g, 45 mmol) and diethylzinc (29.5 mL of a 1.1 M solution in toluene, 32.4 mmol). The mixture was degassed and then there was added POPd (Combiphos) (0.27 g, 0.54 mmol). The resulting solution was heated at 120° C. in a sealed tube for 18 h. The mixture was allowed to cool and was diluted with water and extracted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concnentrated in vacuo. The residue was purified (ISCO, elution with 0-25% EtOAc/hexane) to afford 3.7 g (75%) of the title compound as an oil. LRMS (ESI): 274.2 (M+H)+.

Workup

customThe mixture was degassed
additionthere was added POPd (Combiphos) (0.27 g, 0.54 mmol)
temperatureto cool
additionwas diluted with water
extractionextracted with ethyl acetate
washThe organics were washed with water and brine
dry with materialdried (MgSO4)
customThe residue was purified
wash(ISCO, elution with 0-25% EtOAc/hexane)

Sources & evidence

ORD record: ord-122a7e1a590b482e8ebf4921ce2eb653
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572805B2

Reaction notes

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