Dimethylformamide → N-methyl-2,6-dinitro-4-(trifluoromethyl)aniline

HRID 533645Notes

Reaction equation

HRID 533645 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][N:19](C=O)C.CN>O>[N+:15]([C:3]1[CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:19][CH3:18])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6329MethylamineHCID 98094-Chloro-3,5-dinitrobenzotrifluoride

Product 1

HCID 5072295N-methyl-2,6-dinitro-4-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-chloro-1,3-dinitro-5-trifluoromethyl-benzene (20 g) and DMF (30 mL), 40% of aqueous methylamine solution (15 mL) was added dropwise under ice-cooling. The mixture was stirred for 6 hours under ice-cooling, and then the reaction mixture was added to iced water. The precipitated powder was collected by filtration, and washed with water to give 20 g of (2,6-dinitro-4-trifluoromethyl-phenyl)-methyl-amine.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. filtrationThe precipitated powder was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-1c857893118b45fdbdb1c25df143a30f
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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