Dimethylformamide → (2-Chloro-6-nitro-4-trifluoromethylphenyl)-methylamine

HRID 923804Notes

Reaction equation

HRID 923804 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].CN(C=O)C.[Cl:21]N1C(=O)CCC1=O>O>[Cl:21][C:8]1[CH:7]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[NH:2][CH3:1]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 88405Benzenamine, N-methyl-2-nitro-4-(trifluoromethyl)-

Product 1

HCID 67981579(2-Chloro-6-nitro-4-trifluoromethylphenyl)-methylamineYield 77.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl-(2-nitro-4-trifluoromethylphenyl)-amine (4.40 g) and DMF (20 ml), N-chlorosuccinimide (3.67 g) was added under ice-cooling, and stirred for 3 hours. The mixture was heated to room temperature, and allowed to stand. Water was poured thereinto under ice-cooling, and then the precipitated solid was collected by filtration. The obtained solid was washed with water, and dried to give 3.96 g of (2-chloro-6-nitro-4-trifluoromethylphenyl)-methylamine.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperatureunder ice-cooling
  4. filtrationthe precipitated solid was collected by filtration
  5. washThe obtained solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-d42508c3ab8d4f5b91e01797cc0e1b9c
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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