Hydrochloric Acid → HCID 22754324, compound

HRID 2071392Notes

Reaction equation

HRID 2071392 reaction equation
P(Cl)(Cl)([Cl:3])=O.C1C2NC3C(=CC=CC=3)OC=2C=CC=1.N1CCCC1=O.[N:26]1[CH2:30][CH2:29][CH2:28][C:27]=1[N:31]1[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[O:38][C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2.Cl>C(O)C.CCOCC.ClCCCl>[ClH:3].[N:26]1[CH2:30][CH2:29][CH2:28][C:27]=1[N:31]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=2[O:38][C:39]2[C:44]1=[CH:43][CH:42]=[CH:41][CH:40]=2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 67278PhenoxazineHCID 2275430610-(3,4-Dihydro-2H-pyrrol-5-yl)-10H-phenoxazine

Product 1

HCID 22754324HCID 22754324, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Phosphorus oxychloride (3.8 g., 0.025 mole) is added in one portion to a mixture of phenoxazine (4.6 g., 0.025 mole) and 2-pyrrolidinone (2.1 g., 0.025 mole) in 50 ml. of 1,2-dichloroethane at 25° C. After stirring the reaction mixture for 15 hr., the reaction mixture is quenched in a mixture of 30 ml. of 5N sodium hydroxide and 30 g. of crushed ice. The organic layer is separated, extracted with 100 ml. of 1.5N hydrochloric acid, made basic with sodium hydroxide and extracted with ether. After drying the ethereal extract over magnesium sulfate and concentrating, the residue thus obtained is crystallized from n-heptane to provide 4.2 g. of 10-(1-PYRROLIN-2-YL)PHENOXAZINE free base, m.p. 110°-113° C. The free base taken up in ethanol, acidified with ethanolic hydrogen chloride and diluted with ether provides a 37% yield of 10-(1-PYRROLIN-2-YL)PHENOXAZINE HYDROCHLORIDE as a monohydrate, m.p. 214°-217° C. (corr.).

Workup

  1. customat 25° C
  2. custom, the reaction mixture is quenched in a mixture of 30 ml
  3. customThe organic layer is separated
  4. extractionextracted with 100 ml
  5. extractionextracted with ether
  6. customAfter drying the ethereal
  7. extractionextract over magnesium sulfate
  8. concentrationconcentrating
  9. customthe residue thus obtained
  10. customis crystallized from n-heptane
  11. customto provide 4.2 g

Sources & evidence

ORD record
ord-7a66e6e743a441178443a1ead31a0954
Source dataset
uspto-grants-1977_09
Patent number
US04046891

Reaction notes

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