4-Methylpyridine → 4-Nonadecylpyridine

HRID 1159738

반응식

HRID 1159738 반응식
[NH2-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[CH2:10](Cl)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)(Cl)Cl>[CH2:3]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

참가 물질

5

반응물 3

HCID 79634-MethylpyridineHCID 188151-ChlorooctadecaneHCID 24533Sodium amide

생성물 1

HCID 45203574-Nonadecylpyridine수율 43%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
60 °C

실험 절차

Into a 300-mL flask equipped with a mechanical stirrer, N2 inlet, pressure-equalizing addition funnel which is thermostated in oil bath, were added 14.8 g of sodium amide (0.38 mol) and 64.0 mL of 4-methylpyridine (61.1 g, 0.656 mol). The mixture was stirred under N2 for 1 h while a color change to deep red was observed. A 110-mL sample of n-octadecyl chloride (95.0 g; 0.33 mol) was added to the rapidly stirred reaction mixture over a period of 1.5 h. Shortly after addition was begun, the reaction mixture was warmed to 60° C. to prevent solidification and was subsequently stirred overnight at 100° C. The reaction mixture was cooled to room temperature, diluted with 200 mL of chloroform, washed three times with 200 mL of H2O, and reduced to dryness with the rotary evaporator. The resultant dark brown product was vacuum distilled three times at 0.07 mmHg to finally afford 48.8 g of constant-boiling (180° C. (0.07 mmHg)), white, waxy solid (0.141 mol, 43% yield based on n-octadecyl chloride). Anal. Calcd for C24H43N: C, 83.41; H, 12.54; N, 4.05. Found: C, 83.6; H, 12.7; N, 4.0. MS (ESIMS): m/z: 345.3.

후처리

  1. customInto a 300-mL flask equipped with a mechanical stirrer, N2 inlet, pressure-equalizing addition funnel which
  2. additionShortly after addition
  3. waitwas subsequently stirred overnight at 100° C
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed three times with 200 mL of H2O
  6. customreduced to dryness with the rotary evaporator
  7. distillationdistilled three times at 0.07 mmHg to finally afford 48.8 g of constant-boiling (180° C. (0.07 mmHg))

출처 및 근거

ORD 기록
ord-b532fa6c1fde47a48defcc9a0789bb83
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812251B2

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