Acetic Acid → HCID 68428569, compound

HRID 639153Notes

Reaction equation

HRID 639153 reaction equation
O=[C:2]([CH3:13])[CH2:3][C:4]([O:6][CH2:7][CH2:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=[O:5].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(O)(=O)C>C1C=CC=CC=1>[F:14][C:15]([F:23])([F:24])[C:16]1[CH:17]=[C:18]([NH:19][C:2]([CH3:13])=[CH:3][C:4]([O:6][CH2:7][CH2:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=[O:5])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 11481114HCID 11481114, compound

Product 1

HCID 68428569HCID 68428569, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3.75 g (1.5 mmol) of the compound of Example 39A in 55 ml benzene are added 3 g (18.5 mmol) 3-(trifluoromethyl)aniline and 1.1 g (18.5 mmol) acetic acid. The mixture is stirred under reflux overnight 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: 6). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. temperatureunder reflux overnight
  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: 6)
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23be09f0ebbe4a5ca5da31755317afe4
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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