4-Methylpyridine → 1-[4-(4-Butyl-phenyl)-butyl]-4-methyl-pyridinium bromide

HRID 84331

반응식

HRID 84331 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N+:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

참가 물질

4

반응물 2

HCID 79634-MethylpyridineHCID 198479361-(4-Bromo-butyl)-4-butyl-benzene

생성물 1

HCID 247809381-[4-(4-Butyl-phenyl)-butyl]-4-methyl-pyridinium bromide수율 72%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-(4-Bromo-butyl)-4-butyl-benzene (1 mmol) was added to a solution of 4-picoline (3 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in a vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no picoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (72%). 1HNMR (300 MHz, CDCl3, ppm), 9.22 (d, J=6.6, 2H), 7.79 (d, J=6.6, 2H), 7.05 (d, J=8.4, 2H), 7.02 (d, J=8.4, 2H), 4.90 (t, J=7.5, 3H), 2.51-2.63 (m, 7H), 1.96-2.06 (m, 2H), 1.58-1.68 (m, 2H), 1.51-1.61 (m, 2H), 1.31-1.37 (m, 2H), 0.89 (t, J=7.2, 3H); 13CNMR, 158.91, 144.31, 140.83, 138.30, 128.92, 128.66, 128.45, 61.26, 35.54, 34.95, 34.04, 31.61, 27.95, 22.73, 22.57, 14.33.

후처리

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in a vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no picoline
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

출처 및 근거

ORD 기록
ord-61b3f1a1ee324191a4e463deb7be134f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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