tert-Butylsulfinamide, (S)-(-)- → (NE,S)-N-[[1-(4-chlorophenyl)imidazol-4-yl]methylidene]-2-methylpropane-2-sulfinamide

HRID 57430

반응식

HRID 57430 반응식
[C:1]([S@@:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([CH:20]=O)[N:17]=[CH:16]2)=[CH:11][CH:10]=1.CCOC(C)=O.CCCCCCC>ClCCCl.[O-]S([O-])(=O)=O.[Cu+2]>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:19]=[C:18](/[CH:20]=[N:7]/[S@:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[O:6])[N:17]=[CH:16]2)=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 21899848Ethylacetate heptaneHCID 838830341-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde

생성물 1

HCID 90415295(NE,S)-N-[[1-(4-chlorophenyl)imidazol-4-yl]methylidene]-2-methylpropane-2-sulfinamide수율 28.2%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 111,2-Dichloroethane용매

반응 조건

온도
60 °C

실험 절차

To a suspension of (S)-(−)tert-Butanesulfinamide (2.35 g, 19.4 mmol) and 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde (4 g, 19.4 mmol) in DCE (39 mL) was added CuSO4 (4.63 g, 29.0 mmol). The reaction mixture was heated at 60° C. for 18 hours in a oil bath. A dark brown suspension resulted. The reaction mixture was then cooled to room temperature, filtered through a pad of celite, rinsed with DCM. The solution was then concentrated onto silica gel. Silica gel column chromatography (EtOAc/Heptane 0 to 100%) provided (S,E)-N-((1-(4-chlorophenyl)-1H-imidazol-4-yl)methylene)-2-methylpropane-2-sulfinamide (1.69 g, 5.45 mmol, 28.2% yield) as a light brown solid. LCMS m/z 310.0 (M+H)+, Rt 0.75 min.

후처리

  1. customA dark brown suspension resulted
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered through a pad of celite
  4. washrinsed with DCM
  5. concentrationThe solution was then concentrated onto silica gel

출처 및 근거

ORD 기록
ord-a02c78eb5d294e7cb5773fcd0cb41ece
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

연결된 노트

불러오는 중…