Ethanamine, 2,2,2-trifluoro- → HCID 19784794, compound

HRID 257242Notes

Reaction equation

HRID 257242 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[F:11][C:12]([F:16])([F:15])[CH2:13][NH2:14]>CS(C)=O>[F:11][C:12]([F:16])([F:15])[CH2:13][NH:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 19784794HCID 19784794, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of o-fluoronitrobenzene (1) (7. 05 g, 50 mmol), 2,2,2-trifluoroethylamine (14.85 g, 3 eq.) and DMSO (20 ml) was heated at 120° C. in an autoclave for 24 hrs., then poured onto crushed ice/H2O. The resultant yellow-orange precipitate was collected by filtration, washed with H2O three times and air-dried to give 10.58 g (98% yield) of N-(2,2,2-trifluoroethyl)-2-nitroaniline (4): mp 84°-89° C.; MS m/e 220(m+); 1H NMR (DMSO-d6)δ4.38 (m, 2H), 6.84 (t, 1H, J=7.6 Hz), 7.32 (d, 1H, J=8.7 Hz), 7.62 (t, 1H, J=7.8 Hz) 8.12 (d, 1H, J=8.7 Hz), 8.31 (1H, --NH).

Workup

  1. addition, then poured
  2. filtrationThe resultant yellow-orange precipitate was collected by filtration
  3. washwashed with H2O three times
  4. customair-dried

Sources & evidence

ORD record
ord-4a355065f79741a6bec94eeefcc89ffd
Source dataset
uspto-grants-1993_11
Patent number
US05260488

Reaction notes

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