Dimethylformamide → N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

HRID 1951305Notes

Reaction equation

HRID 1951305 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].[CH3:13][N:14]([CH3:17])[CH:15]=O>C(Cl)(Cl)Cl>[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:13][N:14]([CH3:17])[CH3:15])#[N:10]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 285322-Amino-5-nitrobenzonitrile2×

Product 1

HCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamideYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
170 °C

Procedure

—Fifteen grams of 5-nitroanthranilonitrile (compound 1, 92 mmol) was added to 25 ml of N,N-dimethylformamide in 200 ml of chloroform and the reaction mixture was heated under reflux for 5 hrs at 170° C. After cooling the reaction mixture at room temperature for 30 min and at 4° C. for 1 hr, the solid residue was washed with diethyl ether to give 19.23 g of compound 2 (yield, 96%). 1H-NMR (300 MHz, d6-DMSO): δ 8.48 (s, 1H), 8.27 (s, 1H), 7.38 (s, 1H), 3.06 (s, 3H), 3.17 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureAfter cooling the reaction mixture at room temperature for 30 min
  3. washthe solid residue was washed with diethyl ether

Sources & evidence

ORD record
ord-e3c0a5fac00140fc84e0d195ea00d6f4
Source dataset
uspto-grants-2013_03
Patent number
US08404698B2

Reaction notes

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