N-bromobutanimide → HCID 10850742, compound

HRID 1532597Notes

Reaction equation

HRID 1532597 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:13][C:7]1[C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 10850742HCID 10850742, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4,5-Dichloro-2-nitroaniline (41.0 g, 198 mmol), N-bromosuccinimide (42.86 g, 241 mmol) and N,N-dimethylformamide were combined and heated to 100° C. for 1 h. The mixture was allowed to cool to room temperature and was poured into a flask containing ice water (1 L). The yellow solid was collected and was dissolved in dichloromethane (2 L), resulting in two phases. The organic layer was collected and was dried over magnesium sulfate, filtered and the solvents were removed under reduced pressure using a rotary evaporator to leave 48.62 g (86%) of a brown solid. Anal. Calcd for C6H3BrCl2N2O2: C, 25.21; H, 1.06; N, 9.80. Found: C, 25.32; H, 1.13; N, 9.68.

Workup

  1. temperatureto cool to room temperature
  2. additionwas poured into a flask
  3. customThe yellow solid was collected
  4. dissolutionwas dissolved in dichloromethane (2 L)
  5. customresulting in two phases
  6. customThe organic layer was collected
  7. dry with materialwas dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-db515b792e3b4e80b98bee3eee4d298f
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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