Phenylacetaldehyde → HCID 71457306, compound

HRID 1621187Notes

Reaction equation

HRID 1621187 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>ClCCl.C1(C)C=CC=CC=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>[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 2

HCID 998PhenylacetaldehydeHCID 7680Benzeneacetamide

Product 1

HCID 71457306HCID 71457306, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 65367Trimethylsilyl triflateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a well stirred suspension of 2-phenylacetamide (540 mg, 4 mmol) in dry dichloromethane (2 mL) was added the 2-phenylacetaldehyde (240 mg, 2 mmol) and trimethylsilyltrifluoromethanesulfonate (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 (560 mg, 76%). 1H NMR (400 MHz, DMSO-d6) δ 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). HPLC-MS (ESI): m/z 373.2 (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-004bfbe25959491c894ec82a227f8c29
Source dataset
uspto-grants-2014_07
Patent number
US08772541B2

Reaction notes

Loading…