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

HRID 538192Notes

Reaction equation

HRID 538192 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cl:13]N1C(=O)CCC1=O>CN(C=O)C>[Cl:13][C:6]1[C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 107052972,3,4-Trichloro-6-nitrobenzenamineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,5-dichloro-2-nitro-phenylamine (0.500 g, 2.42 mmol), N-chlorosuccinimide (0.403 g, 3.02 mmol), and DMF (5 mL) was heated to 100° C. for 1 h. After cooling to 23° C., the solution was poured into ice water. The yellow precipitate was collected by filtration and dissolved in dichloromethane. The organic phase was washed with water, dried (MgSO4), filtered, and concentrated to yield the titled compound (0.468 g, 81%). 1H NMR (400 MHz, CDCl3): 8.28 (s, 1H), 6.70 (s, 2H). The compound did not yield MS data.

Workup

  1. temperatureAfter cooling to 23° C.
  2. filtrationThe yellow precipitate was collected by filtration
  3. dissolutiondissolved in dichloromethane
  4. washThe organic phase was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f5311b34017044f694bce4fb02371d6a
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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