Phenothiazine → HCID 20307176, compound

HRID 1678856Notes

Reaction equation

HRID 1678856 reaction equation
[CH3:1][CH:2]1[NH:6][C:5](=O)[CH2:4][CH2:3]1.P(Cl)(Cl)([Cl:10])=O.[CH:13]1[C:26]2[NH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[S:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>ClCCCl>[ClH:10].[CH3:1][CH:2]1[N:6]([C:5]2[CH2:4][CH2:3][CH:2]([CH3:1])[N:6]=2)[C:5]([N:25]2[C:26]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[S:18][C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 7108PhenothiazineHCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 660555-Methyl-2-pyrrolidone

Product 1

HCID 20307176HCID 20307176, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of 5-methyl-2-pyrrolidinone (6.0 g., 0.06 mole), phosphorus oxychloride (9.2 g., 0.06 mole) in 60 ml. of 1,2-dichloroethane is refluxed for 10 min. A solution of phenothiazine (6.0 g., 0.03 mole) in 20 ml. of 1,2-dichloroethane is added at the end of the reflux period and the reaction mixture stirred and refluxed for 20 hr., and then poured onto 20 ml. of 5N potassium hydroxide and 20 g. of crushed ice. The 1,2-dichloroethane layer is separated and extracted with 30 ml. of 1.5N hydrochloric acid and 30 ml. of water removing water soluble by-product 10-[2-(5-methyl-1-pyrrolinyl)]phenothiazine hydrochloride. After drying the 1,2-dichloroethane solution over magnesium sulfate, the 1,2-dichloroethane solution is concentrated and the solid thus obtained stirred with 40 ml. of acetone and filtered. Crystallization of the filtercake from ethanol-ether provides analytically pure 10-[5-METHYL-1-(5-METHYL-1-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]PHENOTHIAZINE HYDROCHLORIDE in a yield of 17%, m.p. 257°-264° C. (corr.).

Workup

  1. temperaturerefluxed for 20 hr
  2. addition, and then poured onto 20 ml
  3. customThe 1,2-dichloroethane layer is separated
  4. extractionextracted with 30 ml
  5. customof water removing water soluble by-product 10-[2-(5-methyl-1-pyrrolinyl)]phenothiazine hydrochloride
  6. dry with materialAfter drying the 1,2-dichloroethane solution over magnesium sulfate
  7. concentrationthe 1,2-dichloroethane solution is concentrated
  8. customthe solid thus obtained
  9. stirringstirred with 40 ml
  10. filtrationof acetone and filtered
  11. customCrystallization of the filtercake from ethanol-ether

Sources & evidence

ORD record
ord-0b6523d7a2bb4f3ab3f87c3c5347ed42
Source dataset
uspto-grants-1978_03
Patent number
US04077959

Reaction notes

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