Methyl iodide → N-ethoxalyl-N-methyl-4-chloro-6-nitro-2-trifluoromethylaniline

HRID 1461259Notes

Reaction equation

HRID 1461259 reaction equation
[C:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([Cl:18])=[CH:11][C:10]=1[C:19]([F:22])([F:21])[F:20])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[CH3:23]I.[H-].[Na+]>CN(C)C=O>[C:1]([N:8]([CH3:23])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([Cl:18])=[CH:11][C:10]=1[C:19]([F:20])([F:21])[F:22])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 199803055-Chloro-2-ethoxalylamino-3-nitrobenzotrifluoride

Product 1

HCID 19980279N-ethoxalyl-N-methyl-4-chloro-6-nitro-2-trifluoromethylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-ethoxalyl-4-chloro-6-nitro-2-trifluoromethylaniline (11 g. 32.3 mmol) and methyl iodide (3.0 ml, 48 mmol) in dry dimethylformamide (DMF, 50 ml) was added in portions sodium hydride (total 1.7 g, 39 mmol). External cooling was used to keep the reaction temperature below 25° C. Stirring was continued at room temperature for 3 h, whereafter the solvent was removed by evaporation in vacuo. The residue was then partitioned between ether and water. The organic phase was washed twice with water, dried over Na2SO4 and evaporated. This treatment left the title compound as an oil, which was processed without further purification.

Workup

  1. temperatureExternal cooling
  2. customthe reaction temperature below 25° C
  3. customwas removed by evaporation in vacuo
  4. customThe residue was then partitioned between ether and water
  5. washThe organic phase was washed twice with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. waitThis treatment left the title compound as an oil, which
  9. customwas processed without further purification

Sources & evidence

ORD record
ord-7a75cf8b2a6a482fadcb91870baa8a3e
Source dataset
uspto-grants-1991_12
Patent number
US05075304

Reaction notes

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