Thionyl Chloride → HCID 13770877, compound

HRID 1249596Notes

Reaction equation

HRID 1249596 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

Conditions

Temperature
0 °C

Procedure

A suspension of 2-(hydroxymethyl)-5-[(phenylmethyl)oxy]-4-oxo-1,4-dihydropyridine (3 g, 12.99 mmole) in chloroform (15 ml) was cooled to 0° C. 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° C. and the white suspended material was filtered, washed with chloroform and hexane and dried in vacuo. The yield of the title compound was 3.65 g.

Workup

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

Sources & evidence

ORD record
ord-2f2d495776084d6587bdad62331efa89
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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