Nitrone → 4-(2'-cyano-4'-bromo-6'-methylphenylazo)-N,N-diethylaniline

HRID 1701271

반응식

HRID 1701271 반응식
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[N:11][C:12]1[CH:22]=[CH:21][C:15]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][CH:13]=1.[CH2:23]=[N:24]O.N1C(C)=CC=CC=1C.[N+](C1C=CC=CC=1)([O-])=O>[Cu]I>[C:23]([C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[N:11][C:12]1[CH:22]=[CH:21][C:15]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][CH:13]=1)#[N:24]

참가 물질

6

반응물 4

HCID 6350NitroneHCID 7416NitrobenzeneHCID 79372,6-LutidineHCID 125255274-[(2,4-dibromo-6-methylphenyl)diazenyl]-N,N-diethylaniline

생성물 1

HCID 203474554-(2'-cyano-4'-bromo-6'-methylphenylazo)-N,N-diethylaniline수율 15.1%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

반응 조건

온도
95 °C

실험 절차

A stirred mixture of 4-(2',4'-dibromo-6'-methylphenylazo)-N,N-diethylaniline (4.25 parts), copper (I) iodide (2.0 parts), formaldoxime trimer (1.75 parts), 2,6-lutidine (2.15 parts), and nitrobenzene (150 parts) was heated to 95° C. for 6 hours when thin layer chromatography showed reaction to be complete. The mixture was cooled, filtered and the nitrobenzene was removed by steam distillation. Crystallisation of the solid product from ethanol gave 4-(2'-cyano-4'-bromo-6'-methylphenylazo)-N,N-diethylaniline (Found: C, 58.2; H, 5.4; Br, 21.7; N, 15.2. C18H19BrN4 requires C, 58.2; H, 5.15; Br, 21.55; N, 15.1%).

후처리

  1. customreaction
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe nitrobenzene was removed by steam distillation
  5. customCrystallisation of the solid product from ethanol

출처 및 근거

ORD 기록
ord-54d85bb108784b8bbeaa97feaa27ce35
출처 데이터셋
uspto-grants-1980_03
특허 번호
US04192800

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