N-bromobutanimide → HCID 10850742, compound

HRID 1167082Notes

Reaction equation

HRID 1167082 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 8,588.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4,5-Dichloro-2-nitroaniline (41.0 g, 1.98 mmol), N-bromosuccinimide (42.86 g, 2.41 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 C6H3BrCI2N2O2: 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-610be7298eee4c538fdd3061c2a18ce6
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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