N,N-Dimethylaniline → HCID 23440323, compound

HRID 2119263Notes

Reaction equation

HRID 2119263 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:10][C:11](I)([C:16](F)(F)[F:17])[C:12]([F:15])([F:14])[F:13].C([O-])(O)=O.[Na+].NC1C=CC=CC=1>O.CN(C)C=O>[F:17][CH2:16][C:11]([F:10])([C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:9])[CH3:1])=[CH:4][CH:5]=1)[C:12]([F:15])([F:14])[F:13]

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 6115AnilineHCID 33978Perfluoroisopropyl iodideHCID 516892Sodium Bicarbonate

Product 1

HCID 23440323HCID 23440323, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4-(Pentafluoroisopropyl)-N,N-dimethylaniline was prepared as follows. A flask was charged with N,N-dimethylaniline (10.2 g), perfluoroisopropyl iodide (25 g), N,N-dimethyl formamide (35 mL) and water (15 mL). To the flask was slowly added a mixture of NaS2O4 (17.5 g) and NaHCO3 (8.5 g). The reaction started immediately when the mixture of NaS2O4/NaHCO3 was introduced, thus the flask was cooled with an ice-water bath. After addition, the mixture was stirred at room temperature overnight. The mixture was poured into 200 mL water. The mixture was then extracted with diethyl ether (4×50 mL). The ether solution was dried over MgSO4. The ether was removed under reduced pressure to give a crude mixture of ortho- and para-substituted perfluoroisopropyl aniline and a bit of the starting aniline (10.0 g). The higher boiling point liquid was distilled to produce a fraction at 38-45° C. (at 0.05 mm Hg) (a mixture of para- and ortho-substituted products as a yellow liquid, 5.5 g). and a fraction at 45-48° C. (at 0.05 mm Hg) (para-substituted perfluoroisopropyl-N,N-dimethylaniline, 3.8 g). The liquid was sampled and analyzed by 1H and 19F NMR. 1H NMR: δ7.35 (d, 2H, J=8 Hz), 6.64 (d, 2H, J=8 Hz), 2.94 (s, 6H); 19F NMR: δ−75.3 (6F), −174.2 (F).

Workup

  1. additionTo the flask was slowly added
  2. additionwas introduced
  3. temperaturethus the flask was cooled with an ice-water bath
  4. additionAfter addition
  5. extractionThe mixture was then extracted with diethyl ether (4×50 mL)
  6. dry with materialThe ether solution was dried over MgSO4
  7. customThe ether was removed under reduced pressure
  8. customto give a crude
  9. distillationThe higher boiling point liquid was distilled
  10. customto produce a fraction at 38-45° C. (at 0.05 mm Hg) (
  11. additiona mixture of para- and ortho-substituted products as a yellow liquid, 5.5 g)
  12. customat 45-48° C.
  13. aliquotThe liquid was sampled

Sources & evidence

ORD record
ord-f74f7513c5bd4fa4802401caffd56db0
Source dataset
uspto-grants-2004_02
Patent number
US06685793B2

Reaction notes

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