Thionyl Chloride → HCID 13435046, compound

HRID 1105805Notes

Reaction equation

HRID 1105805 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[N:11]=[C:12]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][N:13]2[C:14](=[O:19])[C:15]=1[CH2:16][CH2:17][CH3:18].S(Cl)(Cl)=O.O1CCOC[CH2:32]1>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[N:11]=[C:12]2[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:32])=[O:25])=[CH:20][N:13]2[C:14](=[O:19])[C:15]=1[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 13435024HCID 13435024, compound

Product 1

HCID 13435046HCID 13435046, compound

Procedure

2-trans-[2-(2-methyl-phenyl)-ethenyl]-3-propyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-7-carboxylic acid (1,2 g) was reacted with thionyl chloride (0.6 ml) in dioxane (12 ml) at reflux temperature for 1 hour, then the mixture was evaporated to dryness in vacuo. The residue was reacted with excess methanol at 50° C. for 30 minutes, then the solution was concentrated in vacuo and the residue diluted with ice water. Filtration of the precipitate gave 1.2 g of 2-trans-[2-(2-methyl-phenyl)-ethenyl]-3-propyl-4-oxo-4H-pyrido[1,2-a]pyrimidine7-carboxylic acid, methyl ester, m.p. 190°-193° C. By proceeding analogously the following compounds were prepared:

Workup

  1. temperatureat reflux temperature for 1 hour
  2. customthe mixture was evaporated to dryness in vacuo
  3. customThe residue was reacted with excess methanol at 50° C. for 30 minutes
  4. concentrationthe solution was concentrated in vacuo
  5. additionthe residue diluted with ice water
  6. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-a284f1ec92794885bf168693d65390f6
Source dataset
uspto-grants-1982_01
Patent number
US04310526

Reaction notes

Loading…