Dimethylformamide → N-(2'-cyano-4'-nitrophenyl)-4-nitrophthalimide

HRID 1706642Notes

Reaction equation

HRID 1706642 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:25]=[C:22]([C:23]#[N:24])[C:21]([NH2:26])=[CH:20][CH:19]=1)([O-:17])=[O:16].CN(C)C=O.CC(N(C)C)=O>CS(C)=O>[C:23]([C:22]1[CH:25]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=[CH:20][C:21]=1[N:26]1[C:11](=[O:12])[C:6]2=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=[C:7]2[C:8]1=[O:10])#[N:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 285322-Amino-5-nitrobenzonitrileHCID 31374DimethylacetamideHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 20333887N-(2'-cyano-4'-nitrophenyl)-4-nitrophthalimide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Equimolar quantities of 4-nitrophthalic anhydride and 5-nitroanthranilonitrile (Aldrich Chemical Co.) can be heated in a solvent such as dimethylformamide, dimethylacetamide or dimethyl sulfoxide to give N-(2'-cyano-4'-nitrophenyl)-4-nitrophthalimide, which can be isolated and purified by recrystallization. An alternative method of synthesis for this intermediate is the reaction of 2-chloro-5-nitrobenzonitrile with the potassium salt of 4-nitrophthalimide, using one of the solvents listed above.

Sources & evidence

ORD record
ord-711d5d27ec29467685b10ed6ec560227
Source dataset
uspto-grants-1980_06
Patent number
US04208343

Reaction notes

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