Dimethylformamide dimethyl acetal → N'-(6-Cyano-3-methyl-2,4-dinitro-phenyl)-N,N-dimethyl-methanimidamide

HRID 968787Notes

Reaction equation

HRID 968787 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[C:7]([N+:14]([O-:16])=[O:15])=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[C:4]([C:3]1[C:2]([N:1]=[CH:19][N:20]([CH3:22])[CH3:21])=[C:9]([N+:10]([O-:12])=[O:11])[C:8]([CH3:13])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)#[N:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 167267892-Amino-4-methyl-3,5-dinitrobenzonitrile

Product 1

HCID 59016305N'-(6-Cyano-3-methyl-2,4-dinitro-phenyl)-N,N-dimethyl-methanimidamideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-amino-4-methyl-3,5-dinitrobenzonitrile (5) (3.129 g, 14.1 mmol) in anhydrous toluene is added N,N-dimethylformamide dimethyl acetal (4 mL). The resultant mixture is heated to about 100° C. for about 2.5 hours. The mixture is cooled to ambient temperature and the solvent is removed using a rotary evaporator. The residue is dried to provide crude N′-(6-Cyano-3-methyl-2,4-dinitro-phenyl)-N,N-dimethyl-methanimidamide (8) (3.85 g, 99% Yield) as a red solid.

Workup

  1. customthe solvent is removed
  2. customa rotary evaporator
  3. customThe residue is dried

Sources & evidence

ORD record
ord-a1f96b8a5c6e4224acc207c5b9fbab82
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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