Thionyl Chloride → HCID 86690746, compound

HRID 1471692Notes

Reaction equation

HRID 1471692 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[C:12]([CH2:13]O)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:5][CH:4]=[N:3]1.O=S(Cl)[Cl:17]>C(Cl)Cl>[Cl:17][CH2:13][C:12]1[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86690742HCID 86690742, compound

Product 1

HCID 86690746HCID 86690746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol (182 mg, 0.96 mmol) in DCM (5 mL) was added SOCl2 (1.5 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-methyl-1H-pyrazol-5-yl)pyridine (236 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-29e6e11cec354b29b6f99896a48fc926
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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