2-Amino-5-nitrobenzonitrile → N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

HRID 430488Notes

Reaction equation

HRID 430488 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([C:9]#[N:10])[C:7]([NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[C:9]([C:8]1[CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[N:12]=[CH:15][N:16]([CH3:18])[CH3:17])#[N:10]

Participants

3

Reactant 2

HCID 285322-Amino-5-nitrobenzonitrileHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

Procedure

A 40.8 g portion of 5-nitro-anthranilonitrile and 40 ml of N, N-dimethylformamide dimethyl acetal were heated on a steam bath for 2 hours. The solvents were removed at reduced pressure and the residue was taken up in methylene chloride. After passing this solution through Magnesol the solvent was removed. After washing with ether 50.8 g of N′-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine was obtained.

Workup

  1. customThe solvents were removed at reduced pressure
  2. customwas removed
  3. washAfter washing with ether 50.8 g of N′-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine
  4. customwas obtained

Sources & evidence

ORD record
ord-cd883c845d474c7f9909062c05452ed2
Source dataset
uspto-grants-2001_11
Patent number
US06323209B1

Reaction notes

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