Benzene → 5-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one

HRID 1980768

반응식

HRID 1980768 반응식
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([NH:8][NH2:9])=[O:7])([O-:3])=[O:2].[C:14](Cl)(Cl)=[O:15].C1C=CC=CC=1>C(N(CC)CC)C>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]1[O:7][C:14](=[O:15])[NH:9][N:8]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 241BenzeneHCID 6371PhosgeneHCID 3781218o-Nitrobenzohydrazide

생성물 1

HCID 3129215-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

The reactions of Equation 37 above can be run according to similar procedures described in U.S. 4,259,104; Golfier and Milcent, J. Heterocycl. Chem., 10, 989 (1973); and R. Madhavan and V. Srinivasan, Indian J. Chem. 7, 760 (1969). Thus, in reaction 37a, a 2-nitrobenzhydrazide XLVIII is reacted with phosgene in an aprotic solvent such as benzene at ambient temperature for about 10 hours, followed by addition of two mole equivalents of triethylamine and heating at reflux for about 2 hours to form 2-(2-nitrophenyl)-1,3,4-oxadiazolin-5-one of Formula (LI). In reaction 37b, LI is reacted with phosphorus pentachloride in phosphorus oxychloride or with phosphorus pentabromide in phosphorus oxybromide at 25° to 80° C. for about 5 hours to form (Xk'"). And in reaction 37c, Xk'" is reacted with sodium methoxide or sodium ethoxide in a solvent such as methanol or tetrahydrofuran at 0° to 30° C. for about 0.5 to 5 hours to form Xk"".

후처리

  1. temperatureheating
  2. temperatureat reflux for about 2 hours

출처 및 근거

ORD 기록
ord-33f44088e3a94b519d052082d7333448
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04511392

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