Phenylacetaldehyde → HCID 71457306, compound

HRID 1621186Notes

Reaction equation

HRID 1621186 reaction equation
[C:1]1([CH2:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH2:17][CH:18]=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH:8]([NH:10][C:18](=[O:19])[CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 998PhenylacetaldehydeHCID 7680BenzeneacetamideHCID 65367Trimethylsilyl triflate

Product 1

HCID 71457306HCID 71457306, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a well stirred suspension of 2-phenylacetamide (540 mg, 4 mmol) in dry DCM (2 mL) was added the 2-phenylacetaldehyde (240 mg, 2 mmol) and trimethylsilyltrifluoromethane sulfonate (22 mg, 0.1 mmol). The mixture was vigorously stirred for 12 h at room temperature, diluted with toluene (4 mL), and filtered. The precipitate was washed several times with toluene which was recrystallized with methanol and hexane to give the final product (140 mg, 19%). 1H NMR (400 MHz, DMSO-d6) 8.45 (d, J=7.6 Hz, 2H), 7.14-7.28 (m, 15H), 5.55 (t, J=7.6 Hz, 1H), 3.39 (s, 4H), 2.93 (d, J=7.2 Hz, 2H). LC-MS (ESI): m/z 373.0 (M+H)+.

Workup

  1. stirringThe mixture was vigorously stirred for 12 h at room temperature
  2. filtrationfiltered
  3. washThe precipitate was washed several times with toluene which
  4. customwas recrystallized with methanol and hexane

Sources & evidence

ORD record
ord-054c0bb128754a20ad1e667ad69b4771
Source dataset
uspto-grants-2014_07
Patent number
US08772541B2

Reaction notes

Loading…