Formamide → Acetamide, N-(2-(2-(2-cyano-4,6-dinitrophenyl)diazenyl)-5-(diethylamino)phenyl)-

HRID 27679

Reaction equation

Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[N:14]=[N:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:17]=1[NH:27][C:28](=[O:30])[CH3:29].C([O-])(=O)C.[Na+].[CH:36]([NH2:38])=O.C(OC(=O)CC)(=O)CC>[Cu]I.C(OCCCC)(=O)C>[C:36]([C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[N:14]=[N:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:17]=1[NH:27][C:28](=[O:30])[CH3:29])#[N:38]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Bromo-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene (2.4 parts), copper (I) iodide (0.95 parts), anhydrous sodium acetate (1.2 parts), formamide (1.8 parts), propionic anhydride (2.6 parts) and n-butyl acetate (44 parts) are mixed together are heated, with stirring, to 110° C. during 15 minutes. The temperature is maintained for 30 minutes when reaction is adjudged complete by thin layer chromatography. The mixture is cooled to room temperature and poured into petroleum ether (boiling range 60-80° C.) (400 parts). The precipitate is collected, washed with petroleum ether (100 parts) and dried. 2-cyano-4,6-dinitro-2'-acetylamino-4'-(N,N-diethylamino)azobenzene is obtained in 83.5% yield.

Workup

temperatureare heated
temperatureThe temperature is maintained for 30 minutes
customwhen reaction
temperatureThe mixture is cooled to room temperature
customThe precipitate is collected
washwashed with petroleum ether (100 parts)
customdried

Sources & evidence

ORD record: ord-bd6608fb4bfe4cc9af4f818a4bca50c8
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04222935

Linked notes

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