Réaction #1747870

ord-503147315ea649f08e5d68cb04c58034

Équation de réaction

c1ccc(-n2c(-c3ccc(N4c5ccccc5Sc5ccccc54)cc3)nc3ccccc32)cc1
10-[4-(N-phenyl-2-benzimidazolyl)phenyl]phenothiazine
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
[K+].[OH-]
KOH
O=S1(=O)c2ccccc2N(c2ccc(-c3nc4ccccc4n3-c3ccccc3)cc2)c2ccccc21
10-[4-(N-Phenyl-2-benzimidazolyl)phenyl]phenothiazine 5,5-dioxide

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewith cooling
  2. 2
    AutreAfter the methylene chloride had been removed
  3. 3
    workup.ADDITIONthe suspension was diluted with 100 ml of hot water
  4. 4
    FiltrationThe precipitate was filtered off with suction
  5. 5
    Lavagewashed with hot water
  6. 6
    Autredried at 80° C. under reduced pressure
  7. 7
    AutreThe crude product (4.82 g) was recrystallized from 48 ml of acetic acid
  8. 8
    Autrewere obtained

Mode opératoire

A solution of 6.14 g of 10-[4-(N-phenyl-2-benzimidazolyl)phenyl]phenothiazine in 180 ml of methylene chloride was admixed at room temperature with 7.17 g (28.9 mmol) of 70% m-chloroperbenzoic acid with cooling and stirred at room temperature for 1 h. The solution was admixed with 60 ml of 10% KOH. After the methylene chloride had been removed, the suspension was diluted with 100 ml of hot water. The precipitate was filtered off with suction, washed with hot water and dried at 80° C. under reduced pressure. The crude product (4.82 g) was recrystallized from 48 ml of acetic acid. 3.02 g (46% of theory) of beige microcrystals having an m.p. of 286-288° C. were obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08029919B2uspto-grants-2011_10