Reaction #2358560

ord-5de99dc5db1e4000940e1ecbee64932d

Reaction equation

CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=O)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridin-9(10H)-one
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=O)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
compound 11-4
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent
→
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=S)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
title compound
Yield 86.8%
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=S)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H)-thione
Yield 86.8%

Reactants

CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=O)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridin-9(10H)-one
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=O)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
compound 11-4
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for 4 hrs
  2. 2
    OtherToluene was removed by evaporation
  3. 3
    workup.ADDITIONTo the residue methanol (20 mL) was added
  4. 4
    Filtrationthe product was collected by filtration
  5. 5
    Otherdried

Procedure

A mixture of compound 11-4 (560 mg, 1 mmole), anhydrous toluene (10 mL) and Lawesson's reagent (820 mg, 2 mmole) was refluxed for 4 hrs. Toluene was removed by evaporation. To the residue methanol (20 mL) was added, stirred for few minutes at room temperature and the product was collected by filtration and dried to give 500 mg of the title compound. MS 576 (MH+).

Source

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