N-bromobutanimide → 2-Bromo-5-(methylamino)-4-nitrobenzonitrile

HRID 1048993Notes

Reaction equation

HRID 1048993 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]#[N:7].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C.CC(N=NC(C#N)(C)C)(C#N)C.O>[Br:21][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:3]([NH:2][CH3:1])=[CH:4][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 1101939864910-48-1

Product 1

HCID 666848622-Bromo-5-(methylamino)-4-nitrobenzonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6547AzobisisobutyronitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-(methylamino)-4-nitrobenzonitrile (0.9 g, 0.005 mol) and NBS (0.9 g, 0.005 mol) in DMF (15 ml), AIBN (catalytic) was carefully added and the resulting solution was stirred at 80° C. for 3 h. The reaction was diluted with H2O and extracted with dichloromethane (3×30 ml). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound 2-bromo-5-(methylamino)-4-nitrobenzonitrile as a yellow solid. 1H NMR (400 MHz, CDCl3), δ: 8.44 (s, 1H), 8.04 (bs, 1H), 7.18 (s, 1H), 3.05 (s, 3H). MS (M+1): 256.12.

Workup

  1. extractionextracted with dichloromethane (3×30 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a1919bef5a5a48e0aa61456ed993d6e2
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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