Imidazole → Acetamide, N-(2-(2-(2-cyano-4,6-dinitrophenyl)diazenyl)-5-(diethylamino)phenyl)-
Reaction equation
[NH:1]1C=CN=[CH:2]1.[C:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[N:21]=[N:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=1[N+:32]([O-:34])=[O:33])[N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:8])[CH3:7]>>[C:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[N:21]=[N:22][C:23]1[C:24]([N+:32]([O-:34])=[O:33])=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][C:28]=1[C:2]#[N:1])[N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])(=[O:8])[CH3:7]Participants
Procedure
A stirred mixture of 3-acetylamino-4-(2'-bromo-4',6'-dinitro phenylazo)-N,N-diethylaniline (4.8 parts), copper (I) iodide (2.0 parts), formaldoxime trimer (1.8 parts), imidazole (1.35 parts), and nitrobenzene (100 parts) was heated to 85° C. for 71/2 hours when thin layer chromatography showed reaction to be effectively complete. Isolation of the product by the method of Example 9 gave 3-acetylamino-4-(2'-cyano-4',6'-dinitrophneylazo)-N,N-diethylaniline (infra red spectrum identical with that of authenic material). When this experiment was repeated using 3.6 parts of imidazole in place of 1.8 parts a considerable amount of 3-acetylamino-4-(2',4'-dinitrophenylazo)-N,N-diethylaniline was produced in addition to the desired 3-acetylamino-4-(2'-cyano-4',6'-dinitrophenylazo)-N,N-diethylaniline.
Sources & evidence
- ORD record
- ord-3b04499f138a45659ddf158a78085893
- Source dataset
- uspto-grants-1980_03
- Patent number
- US04192800
Reaction notes
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