Pyridine → HCID 12822295, compound

HRID 1112281Notes

Reaction equation

HRID 1112281 reaction equation
O[CH2:2][CH:3]1[CH2:7][NH:6][C:5](=[O:8])[C:4]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:23])=O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:23][CH2:2][CH:3]1[CH2:7][NH:6][C:5](=[O:8])[C:4]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 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 12822291HCID 12822291, compound

Product 1

HCID 12822295HCID 12822295, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 30.0 g. (0.11 mole) of 4-(hydroxymethyl)-3,3-diphenyl-2-pyrrolidinone in 200 ml. of chloroform was added 25.0 g. (0.20 mole) of thionyl chloride. To this stirring solution was added dropwise with ice bath cooling 20.0 g. (0.26 mole) of dry pyridine maintaining room temperature. The solution was refluxed for 2.5 hours. Upon cooling, the chloroform solution was washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution. The chloroform was dried, filtered and concentrated in vacuo. The solid residue was recrystallized twice from ethyl acetate-isopropanol to give product melting at 218°-219° C.

Workup

  1. additionTo this stirring solution was added dropwise with ice bath
  2. temperaturecooling 20.0 g
  3. temperatureThe solution was refluxed for 2.5 hours
  4. temperatureUpon cooling
  5. washthe chloroform solution was washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution
  6. dry with materialThe chloroform was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid residue was recrystallized twice from ethyl acetate-isopropanol

Sources & evidence

ORD record
ord-a54223bc18e946f69a47108cdc62d014
Source dataset
uspto-grants-1978_10
Patent number
US04120969

Reaction notes

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