Thionyl Chloride → ethyl 2-(5-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate hydrochloride

HRID 1471752Notes

Reaction equation

HRID 1471752 reaction equation
O[CH2:2][C:3]1[C:4]([C:9]2[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[CH:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.O=S(Cl)[Cl:22]>C(Cl)Cl>[ClH:22].[Cl:22][CH2:2][C:3]1[C:4]([C:9]2[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[CH:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86690789ethyl 2-(5-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 86690791ethyl 2-(5-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 2-(5-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate (182 mg, 0.70 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 ethyl 2-(5-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate hydrochloride (220 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-550031326fe14ab69a7484c6c5a886e7
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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