Phenothiazine → HCID 13238937, compound

HRID 348384Notes

Reaction equation

HRID 348384 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][N:17]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

7

Reactant 4

HCID 7108PhenothiazineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 2211262-Iodopyridine

Product 1

HCID 13238937HCID 13238937, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

To start with, 2.35 g (11.8 mmol) of phenothiazine (product of Tokyo Kasei Kogyo Co., Ltd.), 3.63 g (17.7 mmol) of 2-iodopyridine (product of Tokyo Kasei Kogyo Co., Ltd.), 6.5 g of potassium carbonate, 1.5 g of copper powder, and 0.31 g of 18-crown-6-ether were mixed with the use of 20 ml of o-dichlorobenzene as a solvent, followed by reflux under a nitrogen atmosphere for 16 hours. After that, copper and inorganic salt were removed and then column purification using a toluene solvent was performed to give a ligand ppt (10-(2-pyridyl)phenothiazine) (opaque white powder; yield: 70%). A summary of the synthesis scheme is shown in the following (a-1).

Workup

  1. temperatureby reflux under a nitrogen atmosphere for 16 hours
  2. customAfter that, copper and inorganic salt were removed
  3. customcolumn purification

Sources & evidence

ORD record
ord-4032f55d645943beae291fa9439de2c9
Source dataset
uspto-grants-2007_02
Patent number
US07176307B2

Reaction notes

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