Sodium Methoxide → HCID 21540629, compound

HRID 1075725Notes

Reaction equation

HRID 1075725 reaction equation
[CH2:1]([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)[CH:5]=1)[CH3:2].C[O-].[Na+].[CH3:21][O:22]NC1C=CC=CC=1>CO>[CH2:1]([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:22][CH3:21])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12441905N-MethoxyanilineHCID 215406005-Chloro-N-ethyl-2-nitro-4-(trifluoromethyl)benzenamine

Product 1

HCID 21540629HCID 21540629, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
119 °C

Procedure

A solution of 14.0g. (0.052 mole) of N-ethyl-3-chloro-6-nitro-4-trifluoromethylaniline and 16.98g. (0.057 mole) of 18.23% methanolic sodium methoxide in 25 ml. of anhydrous methanol was sealed in a glass tube and heated at 119°C. for 88 hours. Removal of the solvent by distillation left a yellow solid residue which was triturated with hot chloroform. Filtration and evaporation of chloroform from the filtrate gave a crude solid residue. Crystallization of the residue from ethanol gave 12.4g. of yellow crystalline product, m.p. 140.5°-141.5°C. shown by its nmr spectrum to be the desired methoxyaniline.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation
  3. waitleft a yellow solid residue which
  4. customwas triturated with hot chloroform
  5. filtrationFiltration and evaporation of chloroform from the filtrate
  6. customgave a crude solid residue
  7. customCrystallization of the residue from ethanol
  8. customgave 12.4g

Sources & evidence

ORD record
ord-02587586333b4a38955c6b932ecfd40e
Source dataset
uspto-grants-1976_05
Patent number
US03954438

Reaction notes

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