Ibuprofenamide → 2-(4-Isobutylphenyl)propiononitrile

HRID 2242922

반응식

HRID 2242922 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([NH2:14])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1.ClC(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]#[N:14])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

참가 물질

4

반응물 2

HCID 101072IbuprofenamideHCID 19083224Phosgen toluene

생성물 1

HCID 1083742-(4-Isobutylphenyl)propiononitrile수율 80%

시약·촉매·용매 1

HCID 22987606Toluene trichloromethane용매

실험 절차

4-isobutyl-α-methylphenylacetamide (2 g; 9.7 mmol), prepared according the procedure described in WO 00/24710, is dissolved in a solution (2:1) toluene/trichloromethane (30 mL). 20% in toluene phosgene (15.5 mL, 30 mmol) is added and the resulting mixture is left stirring 12 h under inert atmosphere until the complete disappearance of the starting reagent. After solvents evaporation under reduced pressure, the crude is dissolved in ethyl acetate (20 mL), the organic phase is washed with a saturated solution of NaHCO3 (2×20 mL) and with a saturated solution of NaCl (2×15 mL), dried over Na2SO4 and evaporated under vacuum to give 2-(4-isobutylphenyl)propionitrile as colourless oil (1.45 g; 7.76 mmol). Yield 80%. 1H-NMR (CDCl3): δ 7.42 (d, 2H, J=7 Hz); 7.28 (d, 2H, J=7 Hz); 4.05 (q, 1H, J=8 Hz); 2.65 (d, 2H, J=8 Hz); 1.95 (m, 1H); 1.80 (d, 3H, J=8 Hz); 1.05 (d, 6H, J=8 Hz).

후처리

  1. waitthe resulting mixture is left
  2. customAfter solvents evaporation under reduced pressure
  3. dissolutionthe crude is dissolved in ethyl acetate (20 mL)
  4. washthe organic phase is washed with a saturated solution of NaHCO3 (2×20 mL) and with a saturated solution of NaCl (2×15 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-d4445f8854d54a9997cff64c9f09902d
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674806B2

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