Acetic Acid → HCID 68425665, compound

HRID 639154Notes

Reaction equation

HRID 639154 reaction equation
O=[C:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[F:9][C:10]([F:19])([F:18])[C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].C(O)(=O)C>C1C=CC=CC=1>[F:9][C:10]([F:18])([F:19])[C:11]1[CH:12]=[C:13]([NH:14][C:2]([CH3:8])=[CH:3][C:4]([O:6][CH3:7])=[O:5])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 7757Methyl acetoacetate

Product 1

HCID 68425665HCID 68425665, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3.48 g (30 mmol) methyl 3-oxobutanoate in 90 ml benzene are added 4.83 g (30 mmol) 3-(trifluoromethyl)aniline and 1.80 g (30 mmol) acetic acid. The mixture is stirred at reflux for four hours using a Dean-Stark trap to remove water. After removal of the solvent in vacuo, the residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 900 μl ethanol solution; number of injections: 8). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. temperatureat reflux for four hours
  2. customto remove water
  3. customAfter removal of the solvent in vacuo
  4. customthe residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 900 μl ethanol solution; number of injections: 8)
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa57b2374b96462890570567dd5d6d46
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

Loading…