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

HRID 495049

Reaction equation

HRID 495049 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-).

Workup

  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

Sources & evidence

ORD record
ord-60690913a7724bd09dfd2b0267e0b481
Source dataset
uspto-grants-2009_05
Patent number
US07538225B2

Linked notes

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