Phenothiazine → 10-(4-Methylphenyl)phenothiazine

HRID 2287295Notes

Reaction equation

HRID 2287295 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>S([O-])([O-])(=O)=O.[Cu+2].C(C1C=CC=CC=1C(C)C)(C)C>[C:19]1([CH3:22])[CH:20]=[CH:21][C:16]([N:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:6][C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 7108PhenothiazineHCID 11430Potassium CarbonateHCID 122074-Iodotoluene

Product 1

HCID 172985110-(4-Methylphenyl)phenothiazineYield 75.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 11345Bis(1-methylethyl)benzeneSolvent

Procedure

A mixture of 25 g (0.126 mol) of phenothiazine, 33 g (0.151 mol) of p-iodotoluene, 4 g (0.025 mol) of copper sulfate, 23 g of potassium carbonate, and 200 ml of diisopropylbenzene was reacted at 180° C. for 3 hours and then at 200° C. for 1 day. The mixture was then cooled and filtered through a Celite. The filtrate was concentrated, and the residual crystals were recrystallized from an ethanol/ethyl acetate mixed solvent to obtain 27.5 g of 10-p-tolylphenothiazine (4b).

Workup

  1. customwas reacted at 180° C. for 3 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered through a Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residual crystals were recrystallized from an ethanol/ethyl acetate mixed solvent

Sources & evidence

ORD record
ord-e7a3e1c11e4b4c21b88f266bbd6cbc91
Source dataset
uspto-grants-2000_07
Patent number
US06083651

Reaction notes

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