Potassium Carbonate → HCID 88686551, compound

HRID 64777Notes

Reaction equation

HRID 64777 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1)[CH3:3].C[O:19]C1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:27]2)=CC=1.[C:40](=[O:43])([O-:42])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:9]([OH:19])(=[O:13])/[CH:8]=[CH:14]/[C:40]([OH:42])=[O:43].[CH3:1][N:2]([CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[S:27])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1)[CH3:3].[CH3:1][N:2]([CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[S:27])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1)[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87949Lawesson's reagentHCID 136894292-[(dimethylamino)methyl]2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one

Product 1

HCID 88686551HCID 88686551, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of 4.8 g of 2-[(dimethylamino)methyl]2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one in 50 ml of toluene was added 4.9 g of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide. The reaction mixture was kept at reflux for two hours. Concentrated potassium carbonate solution was added which caused separation to give a three-layer system: a toluene layer, an aqueous layer and a gummy layer. Only the toluene and aqueous layer contained the desired free base of the title compound. The layers were separated and the gummy layer was discarded. The aqueous layer was extracted three times with methylene chloride. The methylene chloride extracts after washing with saturated sodium chloride solution were combined with the toluene layer. This organic solution was dried over anhydrous sodium sulfate and evaporated to give 5.25 g of oil. The oil, the free base of the title compound, was dissolved in methanol to which solution was added 2.45 g of fumaric acid. The mixture was heated with stirring and isopropyl alcohol was added to the point of cloudiness and the mixture was stirred overnight. Yellow powder was obtained, 2.85 g, which was recrystallized from methanol, m.p. 178°-179° C.

Workup

  1. temperatureat reflux for two hours
  2. customseparation
  3. customto give a three-layer system

Sources & evidence

ORD record
ord-ba80817353b042f8ae39403d5f4c8a43
Source dataset
uspto-grants-1986_09
Patent number
US04610819

Reaction notes

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