Pyridine → HCID 12822292, compound

HRID 614277Notes

Reaction equation

HRID 614277 reaction equation
O[CH:2]1[CH2:6][N:5]([CH3:7])[C:4](=[O:8])[C:3]1([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.S(Cl)(Cl)=O.N1C=CC=CC=1.[CH:31](Cl)(Cl)[Cl:32]>>[Cl:32][CH2:31][CH:2]1[CH2:6][N:5]([CH3:7])[C:4](=[O:8])[C:3]1([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 20544133HCID 20544133, compound

Product 1

HCID 12822292HCID 12822292, compoundYield 59%

Procedure

To 25.0 g. (0.09 mole) of 4-hydroxy-1-methyl-3,3-diphenyl-2-pyrrolidinone, in 200 ml. of chloroform was added 21.4 g. (0.18 mole) of thionyl chloride. With stirring and ice bath cooling, 18.0 g. (0.23 mole) of pyridine was added dropwise. The solution was refluxed for two hours. After concentrating in vacuo, the residue was dissolved in chloroform and washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide. The chloroform solution was dried, filtered, and concentrated in vacuo. The solid residue was recrystallized from a 50:50 ethyl acetate-isopropyl ether mixture. It weighed 16.0 g. (59% yield) and melted at 120°-122° C.

Workup

  1. temperatureice bath cooling
  2. temperatureThe solution was refluxed for two hours
  3. concentrationAfter concentrating in vacuo
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed successively with dilute hydrochloric acid solution and dilute sodium hydroxide
  6. dry with materialThe chloroform solution was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid residue was recrystallized from a 50:50 ethyl acetate-isopropyl ether mixture

Sources & evidence

ORD record
ord-51738b8f239345ff97091d62973c6fa5
Source dataset
uspto-grants-1979_03
Patent number
US04144245

Reaction notes

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