Chloroform → HCID 85539028, compound

HRID 1252640Notes

Reaction equation

HRID 1252640 reaction equation
OC[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.[CH:22](Cl)(Cl)[Cl:23]>>[ClH:20].[Cl:23][CH2:22][N:4]1[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7](=[O:9])[CH:8]=[CH:3]1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

Product 1

HCID 85539028HCID 85539028, compound

Conditions

Temperature
0 °C

Procedure

A suspension of 1,4-dihydro-2-(hydroxymethyl)5-(phenylmethoxy)-4-pyridinone (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-89ec0ff4302846708d0bdcb1cd3f39e8
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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