Thionyl Chloride → 3-(3-Pyridyl)-2-propynyl chloride hydrochloride

HRID 584167Notes

Reaction equation

HRID 584167 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][CH2:13]O)[CH:6]=1>ClCCl>[ClH:3].[Cl:3][CH2:13][C:12]#[C:11][C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12181442HCID 12181442, compound

Product 1

HCID 694194203-(3-Pyridyl)-2-propynyl chloride hydrochlorideYield 154.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (11.9 g) was added dropwise to a solution of 3-(3-pyridyl)-2-propyn-1-ol (13.3 g) in dichloromethane (266 ml) at room temperature. After completion of the addition, the mixture was stirred for 2 hours at room temperature. The resulting precipitates were collected by filtration and washed with diethyl ether to give 1-chloro-3-(3-pyridyl)-2-propyne hydrochloride (14.5 g) as brownish crystals.

Workup

  1. additionAfter completion of the addition
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-64bf7a11ef6e40c4b91f4092c9452527
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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