Phenothiazine → HCID 21863575, compound

HRID 898092Notes

Reaction equation

HRID 898092 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.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:11]1[C:12]2[N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:13]3[C:14]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[S:6][C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 7108PhenothiazineHCID 123681,6-DibromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 21863575HCID 21863575, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of phenothiazine (0.15 mol), 0.1 mol of 1,6-dibromohexane, 0.15 mol of potassium hydroxide and 1% w/w of tetra-n-butyl ammonium hydrogen sulfate in 300 ml of dry toluene was stirred and refluxed for 48 hours. The reaction mixture was cooled to room temperature, filtered, and washed thoroughly with water. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The crude product was purified by column chromatography using a mixture of ethyl acetate and hexane in a volume ratio of 1:6 as eluent. The yield of 1,6-di(10H-10-phenothiazinyl)hexane was 85%. The 1H-NMR spectrum of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 1.35-1.50(m, 4H), 1.55-1.90(m, 4H), 3.82(t, 4H), and 6.73-7.19(m, 16H).

Workup

  1. temperaturerefluxed for 48 hours
  2. filtrationfiltered
  3. washwashed thoroughly with water
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe crude product was purified by column chromatography
  7. additiona mixture of ethyl acetate and hexane in a volume ratio of 1:6 as eluent

Sources & evidence

ORD record
ord-d8a06a22f82844548bdb553efdcb1fd3
Source dataset
uspto-grants-2008_04
Patent number
US07351508B2

Reaction notes

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