Chlorosuccinimide → 2,3,4-Trichloro-6-nitrobenzenamine

HRID 1532591Notes

Reaction equation

HRID 1532591 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.[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[Cl: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 31398ChlorosuccinimideHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 107052972,3,4-Trichloro-6-nitrobenzenamineYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4,5-Dichloro-2-nitroaniline (15.2 g, 73.2 mmol), N-chlorosuccinimide (12.2 g, 91.6 mmol) and N,N-dimethylformamide (150 mL) were combined and the resulting orange solution was heated to 100° C. for 1 h. The solution was allowed to cool to room temperature and was poured into a flask containing ice water (1.2 L). The yellow solid was collected and was dissolved in dichloromethane (1.5 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 by rotary evaporation to leave 17.6 g (98%) of a yellow solid. MS (Cl): m/z 239.

Workup

  1. temperatureto cool to room temperature
  2. additionwas poured into a flask
  3. customThe yellow solid was collected
  4. dissolutionwas dissolved in dichloromethane (1.5 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 by rotary evaporation

Sources & evidence

ORD record
ord-b438bcc66596454db4e92b301b647edf
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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