Thionyl Chloride → 5-(Chloromethyl)-2-(1H-pyrazol-1-yl)pyridine

HRID 495049

반응식

HRID 495049 반응식
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.O=S(Cl)[Cl:16]>C(Cl)Cl>[Cl:16][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:11][CH:10]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 15980534(6-(1H-pyrazol-1-yl)pyridin-3-yl)methanol

생성물 1

HCID 166559465-(Chloromethyl)-2-(1H-pyrazol-1-yl)pyridine수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of alcohol (III) (10.5 g, 59.9 mmol) in CH2Cl2 (150 ml), SOCl2 (36 g, 22 ml, 299.6 mmol) was added and the resulting reaction mixture was stirred at room temperature for a period of between 12 to 18 hours. The excess SOCl2 was quenched with saturated aqueous NaHCO3. The resulting mixture was extracted with CH2Cl2 and washed with brine. Removal of solvent gave a compound of formulae (11.15 g, 95% yield) as a white solid. MS-ESI=194.06, 196.06, 1H NMR (ppm): 8.59(H3′, d), 8.43(H6, d), 8.03(H2, d), 7.89(H3, dd), 7.78(H5′, s), 6.50(H4′, t), 4.65(—CH2-).

후처리

  1. customthe resulting reaction mixture
  2. customThe excess SOCl2 was quenched with saturated aqueous NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. washwashed with brine
  5. customRemoval of solvent
  6. customgave a compound of formulae (11.15 g, 95% yield) as a white solid

출처 및 근거

ORD 기록
ord-60690913a7724bd09dfd2b0267e0b481
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538225B2

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