Thionyl Chloride → HCID 67975026, compound

HRID 706652Notes

Reaction equation

HRID 706652 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][CH:5]=1)[CH3:2].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[ClH:14].[Cl:14][CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH3:2])[N:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53393171(6-Ethoxypyridin-2-yl)methanol

Product 1

HCID 67975026HCID 67975026, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

(6-Ethoxypyridin-2-yl)methanol (3.00 g, 19.6 mmol) was dissolved in toluene (0.5M, 40 mL). Thionyl chloride (2.86 ml, 39.2 mmol) was added dropwise, during which a white solid began to precipitate out of solution. The mixture was heated to 65° C. with stirring for 1 hour. The mixture was concentrated and the residue shaken with ether and collected by filtration to afford 2-(chloromethyl)-6-ethoxypyridine hydrochloride (1.2 g, 29% yield).

Workup

  1. customto precipitate out of solution
  2. concentrationThe mixture was concentrated
  3. stirringthe residue shaken with ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ca3e1982b36a4308829b9c902ba63ddb
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…