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

HRID 256238Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]([F:17])([F:16])[C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].C(N(CC)CC)C.[CH2:25](Cl)[CH:26]=[CH2:27]>O>[F:7][C:8]([F:16])([F:17])[C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].[CH2:27]([NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([C:8]([F:16])([F:17])[F:7])[CH:10]=1)[CH:26]=[CH2:25]

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium carbonate (318 g; 3 moles), water (0.5 liter), meta-trifluoromethylaniline (966 g; 6 moles) and triethylamine (20 g; 0.2 mole) were introduced, in an inert atmosphere, into a 2 liter round flask. The reaction medium was heated to a temperature of 50° C. with good stirring. Allyl chloride (230 g; 3 moles) was then introduced over approximately a 4 hour period. The temperature increased from 50° C. to 70° C. during the addition of allyl chloride. The reaction mass was then heated to a temperature of 100° C. for 1 hour before being cooled to about 50° C. After washing with water and phase separation, the organic phase was distilled under vacuum (5,000 Pa). This resulted in the separation of unconverted m-trifluoromethylaniline (540 g; 3.35 moles) from N-allyl-meta-trifluoromethylaniline (367 g; 1.83 moles), which corresponds to a 61% yield based on allyl chloride and a 70% yield based on meta-trifluoromethylaniline. The mass/volume output was 245 gel of reaction medium.

Workup

temperatureThe reaction mass was then heated to a temperature of 100° C. for 1 hour
temperaturebefore being cooled to about 50° C
washAfter washing with water and phase separation
distillationthe organic phase was distilled under vacuum (5,000 Pa)

Sources & evidence

ORD record: ord-59cda60cd9c54aa8b8a23d058dd8a76b
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701560

Reaction notes

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