4-Nitrophenol → N-phenethyl-2-phenylacetamide

HRID 2227877Notes

Reaction equation

HRID 2227877 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([N:19]=[N+]=[N-])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(P(CCCC)CCCC)CCC.C1C([N+]([O-])=O)=CC=C(O)C=1>C(#N)C>[CH2:11]([NH:19][C:8](=[O:10])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 999Phenylacetic AcidHCID 13831TributylphosphineHCID 145976Benzene, (2-azidoethyl)-

Product 1

HCID 138516N-phenethyl-2-phenylacetamideYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an argon-blanketed solution of phenylacetic acid (69 mg, 0.51 mmol) in acetonitrile (3 mL) was added bis(trimethylsilyltrifluoroacetamide) (BSTFA, 400 μL, 1.51 mmol) via syringe. The mixture was stirred for 30 min. after which time solvent, unreacted starting material and the reaction by-products were removed at high vacuum. The colorless residue was redissolved in toluene (5 mL) and phenethyl azide (58 mg, 0.39 mmol) then freshly-distilled tri-n-butylphosphine (98 μL, 0.39 mmol) were added via syringe. While nitrogen evolution was still progressing, p-nitrophenol (55 mg, 0.40 mmol) was added in one portion, imparting a bright yellow color to the solution. The reaction was stirred at 65° C. for 48 h. The reaction mixture was partitioned between satd Na2CO3 solution and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a yellow oil that was purified by flash chromatography (1:1 EtOAc/hexane) to yield 91 mg (98%) of the title compound as a white powder (mp 91-92° C., lit. mp 91-93° C.). Spectral data were identical to those reported in the literature.

Workup

  1. customthe reaction by-products were removed at high vacuum
  2. dissolutionThe colorless residue was redissolved in toluene (5 mL)
  3. stirringThe reaction was stirred at 65° C. for 48 h
  4. customThe reaction mixture was partitioned between satd Na2CO3 solution and ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil that
  9. customwas purified by flash chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-7ca4083d3e444f16b52fbb6d3f4ef1f8
Source dataset
uspto-grants-2002_07
Patent number
US06414173B1

Reaction notes

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