Methyl iodide → Benzenamine, N-methyl-2-nitro-4-(trifluoromethyl)-

HRID 1594506Notes

Reaction equation

HRID 1594506 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[H-].[Na+].CI.[C:19]([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:19][NH:6][C:5]1[CH:7]=[CH:8][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 88405Benzenamine, N-methyl-2-nitro-4-(trifluoromethyl)-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-nitro-4-trifluoromethylaniline (200 mmol, 41.2 g) in DMF (200 mL) cooled to 0° C. was added portionwise NaH (210 mmol, 8.4 g of a 60% suspension in mineral oil) (exothermic, gas evolution). The reaction was allowed to reach ambient temperature for 45 min, then cooled back to 0° C. MeI (220 mmol, 13.7 mL) was added via syringe (exothermic) and the resulting slurry was stirred for 2 h. The reaction mixture was poured into a 1:1 mixture of saturated NaHCO3 and brine (1 L) to provide the product as a bright orange precipitate, which was filtered, washed with water and dried in vacuo. 1H NMR (500 MHz, CDCl3), δ (ppm): 8.52 (d, J=1.2 Hz, 1H), 8.31 (br s, 1H), 7.70 (d, J=8.9 Hz, 1H), 6.98 (d, J=9.2 Hz, 1H), 3.13 (d, J=5.3 Hz, 3H). LC-MS (ESI, Method C): 3.34 min, m/z 221.1 (M+1).

Workup

  1. customto provide the product as a bright orange precipitate, which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried in vacuo
  5. custom3.34 min, m/z 221.1 (M+1)

Sources & evidence

ORD record
ord-fc4c53532e4c4778a50def83e9141887
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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