Phenylacetic Acid → Benzeneacetamide, N-methoxy-

HRID 1769624Notes

Reaction equation

HRID 1769624 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[O:12]([NH2:14])[CH3:13].C(N(CC)CC)C>ClCCl>[CH3:13][O:12][NH:14][C:8](=[O:10])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 326647Benzeneacetamide, N-methoxy-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Introduce into a round-bottomed flask 6.8 g (50 mmol) of phenylacetic acid and 4.6 g (55 mmol) of methoxylamine hydrochloride, 5.55 g (55 mmol) of triethylamine and finally 10.83 g (52.5 mmol) of N,N-dicyclohexylcarbodiimide. Dissolve in 150 cm3 of dichloromethane. Stir for 16 hours at room temperature. Remove the precipitate by means of filtration and wash it with dichloromethane. Treat the filtrate with 100 cm3 of 3% HCl, then with 100 cm3 of water and finally with 100 cm3 of 5% NaHCO3.

Workup

  1. customRemove the precipitate
  2. filtrationby means of filtration
  3. washwash it with dichloromethane
  4. additionTreat the filtrate with 100 cm3 of 3% HCl

Sources & evidence

ORD record
ord-610665a2a6344b2bb8693960422fb5fe
Source dataset
uspto-grants-1995_01
Patent number
US05382593

Reaction notes

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