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

HRID 1701271

Reaction equation

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]

Participants

Conditions

Temperature: 95 °C

Procedure

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%).

Workup

customreaction
temperatureThe mixture was cooled
filtrationfiltered
customthe nitrobenzene was removed by steam distillation
customCrystallisation of the solid product from ethanol

Sources & evidence

ORD record: ord-54d85bb108784b8bbeaa97feaa27ce35
Source dataset: uspto-grants-1980_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04192800

Linked notes

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