Reaction #2358558

ord-47adae46502f4f8782cfec5c646175e4

Reaction equation

Cn1c2ccccc2c(=O)c2ccccc21
10-methylacridin-9(10H)-one
O=S(=O)(O)Cl
chlorosulfonic acid
→
Cn1c2ccc(S(=O)(=O)Cl)cc2c(=O)c2cc(S(=O)(=O)Cl)ccc21
title compound
Yield 99.7%
Cn1c2ccc(S(=O)(=O)Cl)cc2c(=O)c2cc(S(=O)(=O)Cl)ccc21
10-methyl-9-oxo-9,10-dihydroacridine-2,7-disulfonyl dichloride
Yield 99.7%

Reactants

Cn1c2ccccc2c(=O)c2ccccc21
10-methylacridin-9(10H)-one
O=S(=O)(O)Cl
chlorosulfonic acid
—
ice

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas heated
  2. 2
    Temperatureat reflux for 5 hours
  3. 3
    OtherReaction mixture
  4. 4
    Othercondensed
  5. 5
    FiltrationThe yellow precipitate of product was collected by filtration
  6. 6
    Washwashed with water
  7. 7
    Otherdried

Procedure

A mixture of 10-methylacridin-9(10H)-one (4.2 g, 20 mmole) and chlorosulfonic acid (100 mL, 1.5 mole) was heated at reflux for 5 hours. Reaction mixture was then condensed, cooled down to room temperature and poured carefully on 500 g of ice. The yellow precipitate of product was collected by filtration, washed with water and dried to provide 8.1 g of the title compound. This material was used for next step without purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120754B2uspto-grants-2015_09