Thionyl Chloride → HCID 13770877, compound

HRID 1252601Notes

Reaction equation

HRID 1252601 reaction equation
O[CH2:2][C:3]1[NH:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.S(Cl)([Cl:20])=O>C(Cl)(Cl)Cl>[ClH:20].[Cl:20][CH2:2][C:3]1[NH:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

Product 1

HCID 13770877HCID 13770877, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 2-(hydroxymethyl)-5-(phenylmethoxy)-4(1H)-pyridinone (3 g, 12.99 mmole) in chloroform (15 ml) was cooled to 0° under argon and treated with thionyl chloride (6.1 ml, 83.62 mmole). Within several minutes, a homogeneous solution was obtained. After stirring an additional 5 minutes, a cream colored solid precipitated. The cooling bath was removed and the mixture was heated at reflux for 45 minutes. The mixture was cooled to 0° and the white precipitate was filtered, washed with chloroform and hexane and dried in vacuo. The yield of the title compound was 3.65 g.

Workup

  1. temperaturewas cooled to 0° under argon
  2. waitWithin several minutes
  3. customa homogeneous solution was obtained
  4. customprecipitated
  5. customThe cooling bath was removed
  6. temperaturethe mixture was heated
  7. temperatureat reflux for 45 minutes
  8. temperatureThe mixture was cooled to 0°
  9. filtrationthe white precipitate was filtered
  10. washwashed with chloroform and hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-45fc8ecd5612466aab2ddda4f988f5a9
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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