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

HRID 240536Notes

Reaction equation

HRID 240536 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[C:4]([C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[N:1]=[CH:15][N:16]([CH3:18])[CH3:17])#[N:5]

Participants

3

Reactant 2

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

Product 1

HCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamideYield 87.2%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-5-nitrobenzonitrile (30.0 g, 184 mmol) and dimethoxy-N,N-dimethylmethanamine (29.6 mL, 223 mmol) was heated to 100° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and dissolved in dichloromethane. The solution was run through a silica plug washing the plug with ethyl acetate. The filtrate was concentrated under reduced pressure, stirred with ether and filtered to provide the product (35.0 g, 87%) as yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in dichloromethane
  3. washwashing the plug with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5dbd2568eac241eb8ed9e576d7c0f917
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

Loading…