Phenothiazine → Phenothiazine, 10-phenyl-

HRID 1375310Notes

Reaction equation

HRID 1375310 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][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[C:16]1([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:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7108PhenothiazineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2855718-Crown-6

Product 1

HCID 95203Phenothiazine, 10-phenyl-

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of phenothiazine (15 g, 0.075 mol), 23 g (0.11 mol) of iodobenzene, 9.6 g (0.150 mol) of copper powder, 35.3 g (0.26 mol) of potassium carbonate, and 1.98 g (0.0075 mol) of 18-crown-6 in 20 ml of 1,2-dichlorobenzene was reflux under nitrogen for 24 hour. The inorganic components were removed by filtering the hot reaction mixture. The crude product formed crystals from the reaction mixture. The product was purified by recrystallization from methanol. The yield of 10-phenylphenothiazine was 12.4 g (60%). The product had a melting point of 93–94° C. (recrystallized from methanol). A 1H NMR spectrum yielded the following results (100 MHz, CDCl3, δ, ppm): 6.0–6.45 (m, 2H, Ar), 6.68–7.20(m, 6H Ar), 7.22–7.68(m, 5H, Ar).

Workup

  1. temperaturewas reflux under nitrogen for 24 hour
  2. customThe inorganic components were removed
  3. filtrationby filtering the hot reaction mixture
  4. customThe crude product formed crystals from the reaction mixture
  5. customThe product was purified by recrystallization from methanol
  6. customa melting point of 93–94° C. (recrystallized from methanol)
  7. customA 1H NMR spectrum yielded the
  8. customfollowing results (100 MHz, CDCl3, δ, ppm)

Sources & evidence

ORD record
ord-06bd61fa03494196a7a1fd5743f324c4
Source dataset
uspto-grants-2007_01
Patent number
US07169520B2

Reaction notes

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