Thionyl Chloride → 9-Acridinecarbonyl chloride

HRID 1252744Notes

Reaction equation

HRID 1252744 reaction equation
O.[CH:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([C:14]=2[C:16]([OH:18])=O)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>>[CH:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([C:14]=2[C:16]([Cl:21])=[O:18])=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 162116879-Acridinecarboxylic Acid Hydrate

Product 1

HCID 6099609-Acridinecarbonyl chloride

Procedure

A mixture of 9-acridinecarboxylic acid hydrate (7.3 g, 30 mmole), and thionyl chloride (50 ml, 0.685 mole) was heated at reflux in a round bottom flask equipped with a reflux condenser, a drying tube, and a stirring bar. The reaction mixture was heated further for one hour after the dissolution occurred, then cooled and evaporated to remove any excess thionyl chloride. The residue was directly utilized in the subsequent reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in a round bottom flask
  3. customequipped with a reflux condenser, a drying tube, and a stirring bar
  4. temperatureThe reaction mixture was heated further for one hour
  5. dissolutionafter the dissolution
  6. temperaturecooled
  7. customevaporated
  8. customto remove any excess thionyl chloride
  9. customThe residue was directly utilized in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-42b57a35178f4ad19cff2df90b84e27a
Source dataset
uspto-grants-1988_05
Patent number
US04745181

Reaction notes

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