Thionyl Chloride → 9-Acridinecarbonyl chloride

HRID 565129Notes

Reaction equation

HRID 565129 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([C:17]=2[C:19]([OH:21])=O)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1>>[CH:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([C:17]=2[C:19]([Cl:3])=[O:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 94721Acridine-9-carboxylic acid

Product 1

HCID 6099609-Acridinecarbonyl chloride

Procedure

Thionyl chloride (20 me) was added to 2.2 g of 9-acridinecarboxylic acid, followed by heating under reflux for 5 hours. After the thionyl chloride was distilled off under reduced pressure, 20 ml of methylene chloride were added further. Distillation was repeated twice under reduced pressure, whereby 2.4 g of the compound (2) were obtained (yield: stoichiometric).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. distillationAfter the thionyl chloride was distilled off under reduced pressure, 20 ml of methylene chloride
  4. additionwere added further
  5. distillationDistillation

Sources & evidence

ORD record
ord-04998fb71de94a189b2a007f32bb022c
Source dataset
uspto-grants-2001_01
Patent number
US06171520B2

Reaction notes

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