N-bromobutanimide → HCID 20380612, compound

HRID 1448643Notes

Reaction equation

HRID 1448643 reaction equation
[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:12])[C:5]([CH3:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:12][C:4]1[C:5]([CH3:11])=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([Cl:1])[C:3]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 134551024-Chloro-3,5-dinitro-o-xylene

Product 1

HCID 20380612HCID 20380612, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-chloro-3,5-dinitro-o-xylene (4.62 g; 0.02 mol), N-bromosuccinimide (3.90 g; 0.022 mol) and carbon tetrachloride (100 ml) is stirred and heated at reflux for 4 hours. The reaction mixture is then irradiated with a light source (60 watt) and refluxing continued for 2 hours. Next, 100 mg of initiator [2,2-azobis(2-methylpropionitrile)] is added and the mixture refluxed for one more hour. The reaction mixture is then cooled to room temperature and stirred under a light source for 48 hours, and filtered. The filtrate is evaporated to dryness in vacuo, and the solid residue recrystallized twice from ethanol to afford 1.35 g of title product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customThe reaction mixture is then irradiated with a light source (60 watt)
  4. temperaturerefluxing
  5. temperaturethe mixture refluxed for one more hour
  6. stirringstirred under a light source for 48 hours
  7. filtrationfiltered
  8. customThe filtrate is evaporated to dryness in vacuo
  9. customthe solid residue recrystallized twice from ethanol

Sources & evidence

ORD record
ord-2d345f68d081434a8ec31b1b9c62e390
Source dataset
uspto-grants-1979_12
Patent number
US04180679

Reaction notes

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