Phenylacetaldehyde → HCID 71457306, compound

HRID 2206988Notes

Reaction equation

HRID 2206988 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-ea1148568a4d4d06ad8c007f6b4a7da8
Source dataset
uspto-grants-2016_06
Patent number
US09376380B2

Reaction notes

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