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

HRID 2309334Notes

Reaction equation

HRID 2309334 reaction equation
[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]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6371PhosgeneHCID 3781218o-Nitrobenzohydrazide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The reactions of Equation 37 above can be run according to similar procedures described in U.S. Pat. No. 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 temperatures 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"".

Workup

  1. temperatureheating
  2. temperatureat reflux for about 2 hours

Sources & evidence

ORD record
ord-3a69e4ab6d684662a69e31b0b5f22eb3
Source dataset
uspto-grants-1987_09
Patent number
US04695311

Reaction notes

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