Acetone Cyanohydrin → 3-(4-Chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione

HRID 1196407노트

반응식

HRID 1196407 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][C:15]1([CH3:23])[NH:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]1.C(N(CC)CC)C.CC(C)(O)C#N>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH:18]2[C:17](=[O:22])[CH2:16][C:15]([CH3:23])([CH3:14])[NH:20][C:19]2=[O:21])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

참가 물질

6

반응물 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2회HCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 126955936,6-Dimethylpiperidine-2,4-dione

생성물 1

HCID 198981913-(4-Chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione수율 62.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-chloro-2-nitrobenzoyl chloride (4.4 g) in dry dichloromethane (5 ml) was added at 5°-10° C. to a stirred solution of 6,6-dimethylpiperidine-2,4-dione (2.8 g) and triethylamine (2.8 ml) in dry dichloromethane (50 ml) and the mixture was stirred at ambient temperature for 18 hours. Triethylamine (8.4 ml) and acetone cyanohydrin (0.4 ml) were added successively to the solution and the mixture was stirred at ambient temperature for 4 hours. The resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml), dried over sodium sulphate and evaporated under reduced pressure to give a yellow solid which was recrystallised from acetonitrile to give 3-(4-chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione (4 g), mp 162°-162.5° C., as a yellow crystalline solid.

후처리

  1. stirringthe mixture was stirred at ambient temperature for 4 hours
  2. washThe resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow solid which
  6. customwas recrystallised from acetonitrile

출처 및 근거

ORD 기록
ord-cce4e7944be34b27b9fe87c1ed71c64c
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05114461

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