N-Methylaniline → HCID 21329844, compound

HRID 614025Notes

Reaction equation

HRID 614025 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([N:9]=[C:10]=[O:11])([CH3:8])[CH3:7].[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC=CC=1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([NH:9][C:10](=[O:11])[N:18]([CH3:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 21329853HCID 21329853, compound

Product 1

HCID 21329844HCID 21329844, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2.3 g of m-trifluoromethyl-α,α-dimethylbenzyl isocyanate in 5 ml of benzene was added to 1.1 g of N-methylaniline in 5 ml of benzene and the mixture was heated under reflux for 2 hours. After allowing the reaction mixture to cool, the mixture was washed successively with 2N aqueous sodium hydroxide, 2N hydrochloric acid and water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation and the resulting crystals were recrystallized from n-hexane to obtain 2.6 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. washthe mixture was washed successively with 2N aqueous sodium hydroxide, 2N hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation
  7. customthe resulting crystals were recrystallized from n-hexane

Sources & evidence

ORD record
ord-336616cb437a473d89b4821b88cb78ca
Source dataset
uspto-grants-1979_03
Patent number
US04143061

Reaction notes

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