Thionyl Chloride → HCID 178458779, compound

HRID 2236538Notes

Reaction equation

HRID 2236538 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([O:10][CH2:11][CH2:12][CH3:13])=[CH:5][N:4]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([O:10][CH2:11][CH2:12][CH3:13])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178458791HCID 178458791, compound

Product 1

HCID 178458779HCID 178458779, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2-hydroxymethyl-5-propoxy-pyridin-4-ol (5.56 g, 30.3 mmole) and 30 mL of chloroform stirred cooled with an ice bath is added 30 mL of thionyl chloride (x g, 0.x mole). This is stirred for 15 minutes at ice bath temperature and then refluxed for 1 hour. The reaction mixture is cooled, evaporated to dryness in vacuo and then treated with isopropanol. The solid is filtered, washed with fresh isopropanol, then ether and air dried to give an off-white solid, 3.4 g, (48%), m.p. 165-7° C.; MS (ES+): m/z 202.3 (M+H).

Workup

  1. temperaturecooled with an ice bath
  2. stirringThis is stirred for 15 minutes at ice bath temperature
  3. temperaturerefluxed for 1 hour
  4. temperatureThe reaction mixture is cooled
  5. customevaporated to dryness in vacuo
  6. additiontreated with isopropanol
  7. filtrationThe solid is filtered
  8. washwashed with fresh isopropanol
  9. dry with materialether and air dried
  10. customto give an off-white solid, 3.4 g, (48%), m.p. 165-7° C.

Sources & evidence

ORD record
ord-66f1ec9bb0884da8a56ede6feae45b90
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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