3-chloro-N'-(3-nitrobenzoyl)benzohydrazide → [2-(3-Chlorophenyl)-1,3,4-oxadiazol-5-yl]-3-nitrobenzene

HRID 1753340Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][NH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[O:10])=O>O=P(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[N:8][N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of N′1-(3-chlorobenzoyl)-3-nitrobenzene-1-carbohydrazide (0.321 g) in POCl3 (3 mL) was stirred at 90° C. for 24 h. The resulting clear solution was quenched with ice-water, solid obtained was filtered washed with water, dried and analyzed to give [2-(3-chlorophenyl)-1,3,4-oxadiazol-5-yl]-3-nitrobenzene. 1H NMR (DMSO-d6): δ 8.86 (t, 1H, J=1.8 Hz), 8.59 (dt, 1H, J=1.8 and 8.4 Hz), 8.48 (m, 1H), 8.25 (t, 1H, J=1.8 Hz), 8.16 (dt, 1H, J=1.2 and 7.5 Hz), 7.93 (t, 1H, J=8.1 Hz), 7.75 (m, 1H), 7.66 (t, 1H, J=7.5 Hz), LCMS: purity: 86%; MS (m/e): 302 (MH+).

Workup

customThe resulting clear solution was quenched with ice-water, solid
customobtained
filtrationwas filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-591011601d40412ab30e813ac553c700
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162989B2

Reaction notes

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