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

HRID 2100607노트

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HRID 2100607 반응식
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]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 690558204-chloro-N,N-diethyl-2-(trifluoromethyl)benzamideHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 69054131N,N,4-Triethyl-2-(trifluoromethyl)benzamide수율 75%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-122a7e1a590b482e8ebf4921ce2eb653
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572805B2

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