Phosphorus oxychloride → HCID 20454808, compound

HRID 1263165Notes

Reaction equation

HRID 1263165 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 and 20 ml of phosphorus oxychloride was immersed in an oil bath (105°-110°) for 3.5 hrs. 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 Ice % 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 saturated with hydrogen chloride gas and the mixture heated to gentle boiling for 10 minutes. 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; m.p. 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. additionIce % sodium hydroxide was added dropwise
  7. temperaturewas maintained
  8. stirringafter shaking
  9. extractionthe chloroform extract
  10. customwas separated
  11. dry with materialdried (Na2SO4)
  12. temperaturethe solvent saturated with hydrogen chloride gas and the mixture heated to gentle boiling for 10 minutes
  13. filtrationThe mixture was filtered while hot and the precipitate
  14. customdried

Sources & evidence

ORD record
ord-9aaa9a626daa4a258b68889a87551cd1
Source dataset
uspto-grants-1984_06
Patent number
USRE031617

Reaction notes

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