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

HRID 2075284

反応式

HRID 2075284 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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-).

後処理

  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

出典と根拠

ORDレコード
ord-96a092be8c2945b8ba5f3af2f51221bb
出典データセット
uspto-grants-2011_04
特許番号
US07919627B2

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