Isoniazid → 4-(1,3,4-Oxadiazol-2-yl)pyridine

HRID 489626노트

반응식

HRID 489626 반응식
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC(OCC)OCC)C>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[O:8][CH:11]=[N:10][N:9]=2)=[CH:3][CH:4]=1

참가 물질

4

반응물 2

HCID 3767IsoniazidHCID 6101p-Toluenesulfonic acid

생성물 1

HCID 7756364-(1,3,4-Oxadiazol-2-yl)pyridine수율 57,738.301%

시약·촉매·용매 1

HCID 31214Ethyl orthoformate용매

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온도
130 °C

실험 절차

A mixture of the isonicotinic hydrazide (13.7 g, 100 mmol), triethylorthoformate (60 ml) and p-toluenesulfonic acid (30 mg) was heated at 130° C. for 12 hours. Excess triethylorthoformate was removed under vacuum. The residue was crystallized from ethyl acetate to give 2-(4-pyridyl)-[1,3,4]oxadiazole (14.8 g); H1 NMR [(CD3)2SO]: δ 9.46 (1H, s), 8.8 (2H, dd), 7.9 (2H, dd).

후처리

  1. customExcess triethylorthoformate was removed under vacuum
  2. customThe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-ac53cc6f65e244bb950c32bdfaad8881
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977256B2

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