Thioanisole → HCID 57450162, compound

HRID 545114Notes

Reaction equation

HRID 545114 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([S:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]CC2C=CC=CC=2)=[O:16])[S:9][CH:10]=1)=[O:5])[CH3:2].C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([S:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 57450161HCID 57450161, compound

Product 1

HCID 57450162HCID 57450162, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The resultant product (10.7 g) of (55-1) was dissolved in trifluoroacetic acid (30 mL), thioanisole (10.3 mL) was added, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate as an eluent. The solvent was evaporated from the eluent to give the title compound (5.81 g) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-b9607bc2812648baadd072de0d1488ea
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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