Pyridine → 1-Cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinone

HRID 1112279노트

반응식

HRID 1112279 반응식
[CH:1]1([N:7]2[CH2:11][CH:10]([CH2:12]O)[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:29])=O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:29][CH2:12][CH:10]1[CH2:11][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8](=[O:26])[C:9]1([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 128222881-Cyclohexyl-4-hydroxymethyl-3,3-diphenyl-2-pyrrolidinone

생성물 1

HCID 128222931-Cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinone수율 55%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To 60.0 g. (0.17 mole) of 1-cyclohexyl-4-hydroxymethyl-3,3-diphenyl-2-pyrrolidinone in 400 ml. of chloroform was added 48.0 g. (0.40 mole) of thionylchloride with stirring. To this solution was added dropwise with ice bath cooling 40 g. (0.52 mole) of dry pyridine and the solution was refluxed for 2 hours. After concentrating in vacuo the residue was dissolved in chloroform and washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution. The chloroform solution was dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was recrystallized from isopropyl ether and after drying weighed 34.5 g. (55% yield) and melted at 124°-126° C.

후처리

  1. additionTo this solution was added dropwise with ice bath
  2. temperaturecooling 40 g
  3. concentrationAfter concentrating in vacuo the residue
  4. dissolutionwas dissolved in chloroform
  5. washwashed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution
  6. dry with materialThe chloroform solution was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from isopropyl ether
  10. customafter drying

출처 및 근거

ORD 기록
ord-814230fbc098440da3f531ed05ff3cd7
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04120969

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