Methanol → 3,7-Bis(2',2'-diphenylvinyl)-10-p-tolylphenothiazine

HRID 2287297Notes

Reaction equation

HRID 2287297 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([CH:17]=O)=[CH:10][CH:9]=3)=O.[C:26]1([CH:32](P(=O)(OCC)OCC)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:47][C:48]([CH3:51])([O-])[CH3:49].[K+].CO>CN(C=O)C>[C:33]1([C:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:1][C:3]2[CH:4]=[CH:5][C:6]3[N:7]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[C:8]4[C:13]([S:14][C:15]=3[CH:16]=2)=[CH:12][C:11]([CH:17]=[C:47]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:15][CH:16]=2)[C:48]2[CH:51]=[CH:13][CH:8]=[CH:9][CH:49]=2)=[CH:10][CH:9]=4)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10267017Diethyl benzhydrylphosphonateHCID 187044763,7-Diformyl-10-p-tolylphenothiazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 187044733,7-Bis(2',2'-diphenylvinyl)-10-p-tolylphenothiazineYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of DMF were dissolved 2.0 g (5.8 mmol) of 3,7-diformyl-10-p-tolylphenothiazine (2b) and 4.0 g (13.2 mmol) of diethyl diphenylmethylphosphonate (3a). Thereto was gradually added 1.5 g (13.4 mmol) of potassium t-butoxide. After the mixture was reacted overnight, 10 ml of methanol was added thereto. The crystals precipitated were taken out by filtration, dissolved in chloroform, purified by silica gel column chromatography (toluene), and then recrystallized from a chloroform/hexane mixed solvent to obtain 1.48 g of the target compound.

Workup

  1. customAfter the mixture was reacted overnight
  2. customThe crystals precipitated
  3. filtrationwere taken out by filtration
  4. dissolutiondissolved in chloroform
  5. custompurified by silica gel column chromatography (toluene)
  6. customrecrystallized from a chloroform/hexane mixed solvent

Sources & evidence

ORD record
ord-8ef1f08c26b04b1f875d9eac75c9cfcf
Source dataset
uspto-grants-2000_07
Patent number
US06083651

Reaction notes

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