Thionyl Chloride → Pyridine, 3-(chloromethyl)-2-(1-(1-methylethyl)-1H-pyrazol-5-yl)-, hydrochloride (1:2)

HRID 1770787Notes

Reaction equation

HRID 1770787 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[C:14]([CH2:15]O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].O=S(Cl)[Cl:19]>C(Cl)Cl>[ClH:19].[Cl:19][CH2:15][C:14]1[C:9]([C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 896547582-(1-(1-Methylethyl)-1H-pyrazol-5-yl)-3-pyridinemethanol

Product 1

HCID 86690720Pyridine, 3-(chloromethyl)-2-(1-(1-methylethyl)-1H-pyrazol-5-yl)-, hydrochloride (1:2)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol (560 mg, 2.58 mmol) in DCM (10 mL) was added SOCl2 (3.0 mL) at RT. The reaction mixture was stirred at RT for 4 h and concentrated to dryness. The crude solid was suspended in toluene and concentrated to dryness. The process was repeated three times and dried under vacuum to give 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (700 mg) as an off-white solid, which was used for next step without further purification.

Workup

  1. concentrationconcentrated to dryness
  2. concentrationconcentrated to dryness
  3. customdried under vacuum

Sources & evidence

ORD record
ord-037da3ba422444eda188d95c3427ae08
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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