3-(Trifluoromethyl)aniline → 3-(Trifluoromethyl)aniline

HRID 256239Notes

Reaction equation

HRID 256239 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH2:12](Cl)[CH:13]=[CH2:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH2:14]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[CH:13]=[CH2:12]

Participants

6

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 7850Allyl chloride2×HCID 8471Triethylamine

Product 2

HCID 73753-(Trifluoromethyl)anilineHCID 3017247N-Allyl-3-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

Toluene (1,830 g) and m-trifluoromethylaniline (1,127 g; 7 moles) were introduced in an inert atmosphere into a 6 liter round flask. The reaction medium was stirred and heated to a temperature of 110° C. At that temperature, allyl chloride (382.5 g; 5 moles) and triethylamine (506 g; 5 moles) were added in parallel, over approximately 3 hours, with a lead of the order of 10% for allyl chloride. When the addition was complete, the reaction medium was maintained at a temperature of 115° C. for 1 hour and was then cooled to a temperature 30° C. The reaction mass was washed with water (4 washes with a total of 1.3 liter of water), to extract triethylamine hydrochloride. The organic phase was then distilled at atmospheric pressure and then under reduced pressure (<3,000 Pa). This resulted in the separation of toluene and unconverted m-trifluoromethylaniline (460 g; 2.86 moles) from N-allyl-m-trifluoromethylaniline (588 g; 2.92 moles), which corresponds to a 57% yield based on allyl chloride and 70% based on converted m-trifluoromethylaniline.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction medium was maintained at a temperature of 115° C. for 1 hour
  3. temperaturewas then cooled to a temperature 30° C
  4. washThe reaction mass was washed with water (4 washes with a total of 1.3 liter of water),
  5. extractionto extract triethylamine hydrochloride
  6. distillationThe organic phase was then distilled at atmospheric pressure

Sources & evidence

ORD record
ord-c723026c276e488bb360b9115c88b92f
Source dataset
uspto-grants-1987_10
Patent number
US04701560

Reaction notes

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