Methanol → N-(dimethylamino)-2,6-dinitro-3-methoxy-4-trifluoromethylaniline

HRID 263121Notes

Reaction equation

HRID 263121 reaction equation
[CH3:1][N:2]([CH3:21])[NH:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[C:6](Cl)[C:5]=1[N+:18]([O-:20])=[O:19].[CH3:22][OH:23].C[O-].[Na+].[Na+].[Cl-]>O>[CH3:1][N:2]([CH3:21])[NH:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[C:6]([O:23][CH3:22])[C:5]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 10942334Sodium MethoxideHCID 13101276N-dimethylamino-3-chloro-2,6-dinitro-4-trifluoromethylaniline

Product 1

HCID 13101285N-(dimethylamino)-2,6-dinitro-3-methoxy-4-trifluoromethylaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of 5.0 g. (0.015 mole) of N-(dimethylamino)-3-chloro-2,6-dinitro-4-trifluoromethylaniline and 50 ml. of anhydrous methanol was added 3.77 g. (0.015 mole) of a 21.8% methanolic sodium methoxide solution. The resultant mixture was stirred at room temperature for 6 hours and was then refluxed overnight for 16 hours. The methanol was then evaporated under vacuum leaving a yellow-solid residue. To the residue was added 150 ml. of water and the mixture stirred for 30 minutes to dissolve the NaCl and any other water-soluble materials. The mixture was then filtered and the water-insoluble solids were washed well with water. The solids were then dissolved in 30 ml. of refluxing 95% ethanol. On cooling, the product crystallized and was isolated by filtration to give 3.83 g. (77.7%) of a yellow crystalline solid; m.p. 109°-110.5° C. After recrystallization from 95% ethanol, the product melts at 110°-111.5° C.

Workup

  1. temperaturewas then refluxed overnight for 16 hours
  2. customThe methanol was then evaporated under vacuum
  3. customleaving a yellow-solid residue
  4. additionTo the residue was added 150 ml
  5. filtrationThe mixture was then filtered
  6. washthe water-insoluble solids were washed well with water
  7. dissolutionThe solids were then dissolved in 30 ml
  8. temperatureof refluxing 95% ethanol
  9. temperatureOn cooling
  10. customthe product crystallized
  11. customwas isolated by filtration
  12. customto give 3.83 g
  13. customAfter recrystallization from 95% ethanol

Sources & evidence

ORD record
ord-45e994ee1ff44653b242b1a7e7c4024e
Source dataset
uspto-grants-1979_05
Patent number
US04156083

Reaction notes

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