Phosphorus oxychloride → HCID 632909, compound

HRID 1596097Notes

Reaction equation

HRID 1596097 reaction equation
[Br:1][C:2]1[C:3]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=O.P(Cl)(Cl)([Cl:21])=O>>[Br:1][C:2]1[C:3]2[C:4](=[C:5]([Cl:21])[C:17]3[C:12]([N:11]=2)=[C:13]([Br:18])[CH:14]=[CH:15][CH:16]=3)[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 623433HCID 623433, compound

Product 1

HCID 632909HCID 632909, compoundYield 74%

Procedure

A suspension of 7.43 g (20.0 mmol) of 3-bromo-2-(2-bromophenylamino)benzoic acid (XXII) in 19.5 ml (213 mmol) of distilled phosphoryl chloride was heated to reflux for 2.5 h. Subsequently, the excess phosphoryl chloride was distilled off at room temperature under vacuum. The resulting brown oil was dissolved in chloroform, and the solution was added dropwise to ice-cooled diluted aqueous ammonia with stirring. After the mixture had reached room temperature, the phases were separated. The aqueous phase was extracted twice with chloroform, and the combined organic phases were dried over sodium sulfate. The solvent was distilled off under vacuum, and the residue was dried under high vacuum. Fractional sublimation of 7.00 g of raw product under high vacuum yielded 5.5 g (74% of theory) of 4,5-dibromo-9-chloroacridine (XXIII) as an analytically pure yellow solid with a melting point of 195-196° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 h
  3. distillationSubsequently, the excess phosphoryl chloride was distilled off at room temperature under vacuum
  4. dissolutionThe resulting brown oil was dissolved in chloroform
  5. additionthe solution was added dropwise to ice-
  6. temperaturecooled diluted aqueous ammonia
  7. customhad reached room temperature
  8. customthe phases were separated
  9. extractionThe aqueous phase was extracted twice with chloroform
  10. dry with materialthe combined organic phases were dried over sodium sulfate
  11. distillationThe solvent was distilled off under vacuum
  12. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-ea2d25f699344e63af726176731caa3d
Source dataset
uspto-grants-2001_09
Patent number
US06290926B1

Reaction notes

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