Pyridine → HCID 12822294, compound

HRID 614279Notes

Reaction equation

HRID 614279 reaction equation
O[CH2:2][CH:3]1[CH2:7][N:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[C:5](=[O:16])[C:4]1([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)([Cl:31])=O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:31][CH2:2][CH:3]1[CH2:7][N:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[C:5](=[O:16])[C:4]1([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 12822289HCID 12822289, compound

Product 1

HCID 12822294HCID 12822294, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 34.0 g. (0.09 mole) of 4-(hydroxymethyl)-3,3-diphenyl-1-(1-phenylethyl)-2-pyrrolidinone in 200 ml. of chloroform was added 25.0 g. (0.20 mole) of thionylchloride. To this solution with stirring and ice bath cooling was added dropwise, 20.0 g. (0.26 mole) of dry pyridine maintaining the reaction mixture at 25° C. The solution was refluxed for 1.5 hours, concentrated in vacuo and the residue was dissolved in chloroform. The solution was washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution. The chloroform solution was dried, filtered, and concentrated in vacuo. The residue was dissolved in hot isopropyl ether and some isooctane was added. The hot solution was decanted from a gummy residue and the product crystallized from the cooled solution. Seven grams were recrystallized in isopropyl ether to give the product which melted at 115°-120° C.

Workup

  1. temperatureice bath cooling
  2. additionwas added dropwise
  3. customat 25° C
  4. temperatureThe solution was refluxed for 1.5 hours
  5. concentrationconcentrated in vacuo
  6. dissolutionthe residue was dissolved in chloroform
  7. washThe solution was washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution
  8. dry with materialThe chloroform solution was dried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue was dissolved in hot isopropyl ether
  12. additionsome isooctane was added
  13. customThe hot solution was decanted from a gummy residue
  14. customthe product crystallized from the cooled solution
  15. customSeven grams were recrystallized in isopropyl ether
  16. customto give the product which melted at 115°-120° C.

Sources & evidence

ORD record
ord-435a4252a3bc49cd8e6681c9acb3695b
Source dataset
uspto-grants-1979_03
Patent number
US04144245

Reaction notes

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