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

HRID 405338

반응식

HRID 405338 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-197ca6a3ad6b40c1bc0e8c4b2a5dd3e3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748597B2

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