Triethylamine hydrochloride → 3-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazole

HRID 2277846Notes

Reaction equation

HRID 2277846 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.C([N:18](CC)[CH2:19][CH3:20])C.CC[N:25]=C=NCCCN(C)C.Cl.C(N(C(C)C)CC)(C)C>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[O:12][N:25]=[C:19]([CH3:20])[N:18]=2)=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 15720(4-Nitrophenoxy)acetic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 220604453-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazoleYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrophenoxy acetic acid (2.25 g, 11.4 mmole), acetamideoxime, triethylamine hydrochloride (3.85 g, 27.62 mmole), EDCI.HCl (4.37 g, 22.79 mmole) and diisopropylethylamine (7.42 g, 57.40 mmole) in anhydrous THF (250 ml) was refluxed for 18 h. The unhomogenous brown colored reaction mixture was quenched with water and extracted with EtOAc (3×300 mL). The combined organic layers washed successively with aqueous NaHCO3, brine and dried over anhydrous Na2SO4. Removal of solvent and purified by chromatographic purification provided 5-[(4-nitrophenoxy)methyl]-3-methyl-1,2,4-oxadiazole (1.62 g, 60%). 1H NMR (CDCl3): δ 8.24 (d, 2H, J=8.8 Hz), 7.08 (d, 2H, J=8.8 Hz), 5.36 (s, 2H), 2.44 (s, 3H).

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe unhomogenous brown colored reaction mixture was quenched with water
  3. extractionextracted with EtOAc (3×300 mL)
  4. washThe combined organic layers washed successively with aqueous NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customRemoval of solvent
  7. custompurified by chromatographic purification

Sources & evidence

ORD record
ord-007bff3c588042beb4a4af71ef99d78a
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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