N-bromobutanimide → HCID 21264584, compound

HRID 567123Notes

Reaction equation

HRID 567123 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:11])[C:9]#[N:10].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:12][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:11])[C:9]#[N:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 21264592HCID 21264592, compound

Product 1

HCID 21264584HCID 21264584, compoundYield 474.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

22.6 g (0.155 mol) of N-(2-methylphenyl)-N-methyl-cyanamide are dissolved in 300 ml of carbon tetrachloride, admixed with about 5 g of N-bromosuccinimide and 0.1 g of azodiisobutyronitrile and radiated using a UV lamp (250 W) for 5 hours with stirring. Over this period, more N-bromosuccinimide (a total of 32.9 g (0.185 mol)) is added a little at a time. The temperature increases during the reaction, until the solution boils at reflux. The reaction mixture is cooled and filtered, and the filtrate is concentrated under reduced pressure. 30 g of N-(2-bromomethyl-phenyl)-N-methyl-cyanamide of a content of 40% (HPLC) are obtained.

Workup

  1. customfor 5 hours
  2. waitOver this period
  3. temperatureThe temperature increases during the reaction, until the solution
  4. temperatureat reflux
  5. temperatureThe reaction mixture is cooled
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a5ce7e95c73949ee8d6ba0275a4a55b4
Source dataset
uspto-grants-2001_01
Patent number
US06177459B1

Reaction notes

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