Trifluoroacetic acid → (3-Carboxy-4-chloro-phenyl)-trimethyl-ammonium trifluoro-methanesulfonate

HRID 1041878Notes

Reaction equation

HRID 1041878 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][C:11]=1[C:20]([O:22]C)=[O:21].FC(F)(F)C(O)=O>O>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[C:20]([C:11]1[CH:12]=[C:13]([N+:16]([CH3:19])([CH3:18])[CH3:17])[CH:14]=[CH:15][C:10]=1[Cl:9])([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86624965HCID 86624965, compound

Product 1

HCID 50991165(3-Carboxy-4-chloro-phenyl)-trimethyl-ammonium trifluoro-methanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.5 g (1.32 mmol) 18b, 12 ml dest. water and 12 ml trifluoroacetic acid was refluxed for 2 days. The reaction mixture was evaporated, dried by use of oil pump vacuum over night and treated with diethyl ether. The resulting solid was filtered, washed extensively with diethyl ether and dried by oil pump vacuum. The solid crude product 18c was obtained in 98% yield (471 mg, 1.3 mmol) and crude compound 18c was used for the next step without purification.

Workup

  1. customThe reaction mixture was evaporated
  2. customdried by use of oil pump vacuum over night
  3. additiontreated with diethyl ether
  4. filtrationThe resulting solid was filtered
  5. washwashed extensively with diethyl ether
  6. customdried by oil pump vacuum

Sources & evidence

ORD record
ord-a6eff601f427438d8b470b065151b060
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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