Phosphorus trichloride → HCID 21551706, compound

HRID 268216Notes

Reaction equation

HRID 268216 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6](O)[C:7]3[CH2:8][C:9]([CH3:19])([CH3:18])[CH2:10][C:11](=[O:17])[C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[CH2:8][C:9]([CH3:19])([CH3:18])[CH2:10][C:11](=[O:17])[C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 623984HCID 623984, compound

Product 1

HCID 21551706HCID 21551706, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 g (0.066 mole) of 7-chloro-3,3-dimethyl-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9(10H)-acridone were suspended in 320 ml of chloroform and, after heating on a steam bath, combined dropwise with 11.3 ml (0.13 mole) of phosphorus trichloride. Upon cooling, 16 g of 7-chloro-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-9(10H)-acridone crystallized in the form of the hydrochloride. This compound was dissolved in a mixture of 300 ml of methanol and 50 ml of binormal sodium hydroxide solution, the solution was filtered, the filtrate was concentrated under reduced pressure and the base that had crystallized was filtered off with suction. 13.5 g (74 % ) of 7-chloro-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-9(10H)-acridone were obtained. Decomposition point 300° C.

Workup

  1. temperatureafter heating on a steam bath
  2. temperatureUpon cooling
  3. custom16 g of 7-chloro-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-9(10H)-acridone crystallized in the form of the hydrochloride
  4. dissolutionThis compound was dissolved in a mixture of 300 ml of methanol and 50 ml of binormal sodium hydroxide solution
  5. filtrationthe solution was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe base that had crystallized
  8. filtrationwas filtered off with suction

Sources & evidence

ORD record
ord-4f41f9b5960c4745bb726670e5b43d4a
Source dataset
uspto-grants-1976_03
Patent number
US03947449

Reaction notes

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