Hydrochloric Acid → Dimethylanilinium chloride

HRID 1282394Notes

Reaction equation

HRID 1282394 reaction equation
B(F)(F)F.CCOCC.FC1C([Mg]Br)=C(F)C(F)=C(F)C=1F.[ClH:23].[CH3:24][N:25]([CH3:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.C(OCC)C>[Cl-:23].[CH3:24][NH+:25]([CH3:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 8000Boron trifluoride etherateHCID 178505971HCID 178505971, compound

Product 1

HCID 11789467Dimethylanilinium chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

Boron trifluoride diethyl etherate (138.7 g, 0.98 mole) is added to a diethyl ether solution of pentafluorophenylmagnesium bromide (3326 g, 4.17 moles) formed as in Example 24. The addition is at a rate allowing the mixture to reach reflux temperature. The mixture is heated at reflux for 18 hours. This mixture is then cooled to −10° C. and N,N-dimethylanilinium chloride (1142 grams, 2.06 moles) previously formed from concentrated HCl, water, and N,N-dimethylaniline is slowly added while keeping the temperature at about 0° C. After the addition, the mixture is stirred for one hour at −5° C. to 0° C. Then the two phases are separated, and the organic phase is washed with water and dried over MgSO4. The N,N-dimethylanilinium tetrakis(pentafluorophenyl)borane is precipitated by addition of hexane with stirring, and recovered by filtration.

Workup

  1. customformed as in Example 24
  2. additionThe addition
  3. temperatureto reach reflux temperature
  4. temperatureThe mixture is heated
  5. temperatureat reflux for 18 hours

Sources & evidence

ORD record
ord-77eba45b3e2442ee83a4f9bf3316c160
Source dataset
uspto-grants-2002_09
Patent number
US06455718B1

Reaction notes

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