Ethanamine, 2,2,2-trifluoro- → HCID 22025443, compound

HRID 733264Notes

Reaction equation

HRID 733264 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[C:6]2=[O:13].[F:16][C:17]([F:21])([F:20])[CH2:18][NH2:19]>C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(=O)OCC>[F:16][C:17]([F:21])([F:20])[CH2:18][N:19]1[C:6](=[O:13])[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:15])[F:14])[CH:4]=2)[C:8]1=[O:12]

Participants

5

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 127177895-(Trifluoromethyl)isobenzofuran-1,3-dione

Product 1

HCID 22025443HCID 22025443, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of 5-trifluoromethyl-isobenzofuran-1,3-dione were dissolved using 50 ml of toluene(anhydrous) and 4.6 g of 2,2,2-trifluoro-ethylamine added. The mixture was left at ambient temperature for 16 h. 50 mg of toluene-4-sulfonic acid were then added and the mixture was refluxed for 5 h. 200 ml of EA were added and the mixture was washed twice using 50 ml of a 10% aqueous Na2CO3-solution. The organic layer was dried over MgSO4 and the solvent was removed in vacuo to yield 5.5 g of a viscous oil (Rf(DIP)=0.57; MS (EI): 298 (M+1)+).

Workup

  1. additionadded
  2. temperaturethe mixture was refluxed for 5 h
  3. washthe mixture was washed twice
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-08a39e5611d34ee1ac29f9391da919fa
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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