4-tert-Butylbenzonitrile → HCID 70979018, 화합물

HRID 1852248

반응식

HRID 1852248 반응식
C([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[CH3:13])C.[Li]CCCC.[C:22]([C:26]1[CH:33]=[CH:32]C(C#N)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([C:26]1[CH:33]=[CH:32][C:16]([C:15]2[NH:3][C:4](=[O:14])[C:5]3[C:6]([CH:13]=2)=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=3)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]

참가 물질

5

반응물 3

HCID 778834-tert-ButylbenzonitrileHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418339Butyllithium

생성물 1

HCID 70979018HCID 70979018, 화합물수율 51.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (10 ml) was added n-BuLi (2.82 ml, 4.52 mmol, in hexane) at −78° C. and stirred for 1 h. Then to this 4-(tert-butyl)benzonitrile (0.72 g, 4.52 mmol) was added at same temperature and allowed to warm to room temperature and continued the stirring for another 1 h at room temperature. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOac (2*100 ml). The organic phase was washed with brine, dried on Na2SO4, and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (0.72 g, 46.7%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.26(s, 1H), 8.11-8.09 (d, J=8 Hz, 1H), 7.73-7.71 (d, J=8 Hz, 2H), 7.52-7.50 (d, J=8 Hz, 2H), 7.06 (s, 1H), 7.05-7.03 (d, J=8 Hz, 1H), 6.82 (s, 1H), 3.89 (s, 3H), 1.32 (s, 9H); MS: MS m/z 308.2 (M++1).

후처리

  1. customstirring for another 1 h
  2. customat room temperature
  3. customThe reaction mixture was quenched with saturated NH4Cl solution
  4. extractionextracted with EtOac (2*100 ml)
  5. washThe organic phase was washed with brine
  6. customdried on Na2SO4
  7. customevaporated under reduced pressure
  8. customto get crude compound
  9. customThe crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether)

출처 및 근거

ORD 기록
ord-4c73b52e940a4ebda95a89a788bad121
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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