Phosphorus oxychloride → HCID 20454808, compound

HRID 1576761Notes

Reaction equation

HRID 1576761 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=O)[NH:7]2.P(Cl)(Cl)([Cl:21])=O>>[ClH:21].[Cl:21][C:6]1[N:5]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20454780HCID 20454780, compound

Product 1

HCID 20454808HCID 20454808, compoundYield 70%

Procedure

A mixture of 2.45 g (10 mmole) of 5-methyl-3-carbethoxymethyl-1,2,3,4-tetrahydroquinazolin-2-one (IIIc) and 20 ml of phosphorus oxychloride was immersed in an oil bath (105°-110°) for 3.5 hr. The solution was cooled, the excess phosphorus oxychloride removed under aspirator pressure and the residue dissolved in chloroform (50 ml). Ice water was added, the mixture shaken and 40% sodium hydroxide was added dropwise to attain a pH=6. The above process was repeated until a pH=6 was maintained after shaking, the chloroform extract was separated, dried (Na2SO4) and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (100 ml), the solution saturated with hydrogen chloride gas and the mixture heated to gentle boiling for 10 mins. The mixture was filtered while hot and the precipitate dried yielding 2.11 g (70% yield) of a pale yellow powder. Purification was effected by crystallization from acetonitrile; mp 199-201.

Workup

  1. customwas immersed in an oil bath
  2. temperatureThe solution was cooled
  3. customthe excess phosphorus oxychloride removed under aspirator pressure
  4. dissolutionthe residue dissolved in chloroform (50 ml)
  5. additionIce water was added
  6. addition40% sodium hydroxide was added dropwise
  7. temperaturewas maintained
  8. stirringafter shaking
  9. extractionthe chloroform extract
  10. customwas separated
  11. dry with materialdried (Na2SO4)
  12. customthe solvent removed in vacuo
  13. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  14. temperaturethe solution saturated with hydrogen chloride gas and the mixture heated to gentle boiling for 10 mins
  15. filtrationThe mixture was filtered while hot and the precipitate
  16. customdried

Sources & evidence

ORD record
ord-9a9c305aac7f4aac84ea91f1910802d5
Source dataset
uspto-grants-1976_09
Patent number
US03983120

Reaction notes

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