Methanol → 3,7-Bis(2,2-diphenylvinyl)-10-methylphenothiazine

HRID 1660677Notes

Reaction equation

HRID 1660677 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][N:8]1[C:21]2[CH:20]=[CH:19][C:18]([CH:22]=O)=[CH:17][C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([CH:24]=O)[CH:13]=2.[CH:26](P(=O)(OCC)OCC)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CO>CS(C)=O>[C:2]1([C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:24][C:12]2[CH:11]=[CH:10][C:9]3[N:8]([CH3:7])[C:21]4[C:16]([S:15][C:14]=3[CH:13]=2)=[CH:17][C:18]([CH:22]=[C:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:19][CH:20]=4)[CH:3]=[CH:17][CH:16]=[CH:21][CH:1]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 35935810-Methylphenothiazine-3,7-dicarbaldehydeHCID 10267017Diethyl benzhydrylphosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 596095863,7-Bis(2,2-diphenylvinyl)-10-methylphenothiazine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.46 g (30.4 mmol) of potassium tert-butoxide and then 3.60 g (13.4 mmol) of 10-methylphenothiazine-3,7-dicarbaldehyde were added with stirring and at room temperature to a solution of 8.20 g (26.8 mmol) of diethyl benzhydrylphosphonate (prepared analogously to Example 13 in U.S. Pat. No. 5,130,603) in 60 ml of anhydrous dimethyl sulfoxide, in the course of which the temperature rose from 25 to 43° C. After stirring at room temperature for 5 hours, the reaction solution was admixed with 150 ml of methanol, stirred for 15 min and filtered through a black band filter. The residue was washed with 300 ml of methanol and dried at 80° C. under reduced pressure. The crude product (4.7 g) was dissolved in 150 ml of methylene chloride, purified on silica gel and recrystallized from 83 ml of butylglycol. 3.56 g (23% of theory) of greenish microcrystals having a melting point of 233-241° C. were obtained.

Workup

  1. customprepared analogously to Example 13 in U.S
  2. customrose from 25 to 43° C
  3. stirringstirred for 15 min
  4. filtrationfiltered through a black band
  5. filtrationfilter
  6. washThe residue was washed with 300 ml of methanol
  7. customdried at 80° C. under reduced pressure
  8. dissolutionThe crude product (4.7 g) was dissolved in 150 ml of methylene chloride
  9. custompurified on silica gel
  10. customrecrystallized from 83 ml of butylglycol
  11. customwere obtained

Sources & evidence

ORD record
ord-d521502a280947329879582b45a2df58
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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