Water → Ethyl 5-Benzyl-1,2,4-oxadiazole-3-carboxylate

HRID 58622Notes

Reaction equation

HRID 58622 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12](=[N:18]O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)C(C)C)(C)C.O>ClCCl>[CH2:7]([C:8]1[O:9][N:18]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:11]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 51063889Ethyl 5-Benzyl-1,2,4-oxadiazole-3-carboxylateYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-phenyl acetyl chloride (1.0 mL; 7.57 mmol) was added to a mixture of ethyl 2-amino-2-(hydroxyimino)acetate (0.5 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 mmol) in dichloromethane (15 mL) at −15° C. The reaction mixture was stirred at room temperature overnight and poured into a mixture of ice and water. The formed precipitate was filtered off, suspended in pyridine (18 mL) and refluxed in a sealed tube for 20 h and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.308 g (35%) of the title compound as a white solid.

Workup

  1. filtrationThe formed precipitate was filtered off
  2. temperaturerefluxed in a sealed tube for 20 h
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-cd2ad49fd52c44b78ce3e7c3474e5578
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

Loading…