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

HRID 1968639Notes

Reaction equation

HRID 1968639 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]>O1CCOCC1>[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

4

Reactant 2

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

Product 1

HCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-nitroanthranilonitrile (1.00 g, 6.13 mmol) in dioxane (25 mL) was added dimethylformamide dimethyl acetal (0.88 g, 7.36 mmol). Th reaction mixture was stirred at 100° C. for 2 h and then cooled to room temperature and refrigerated. The precipitate was filtered out, washed with cold ether several time, and then dried in vacuo to give 1.30 g (97%) of N′-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered out
  3. washwashed with cold ether several time
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3c67a87daba64e05bcf6c22b7245f35d
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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