4-Chlorobenzoyl chloride → 3-(3-Bromo-thiophen-2-yl)-5-(4-chloro-phenyl)-[1,2,4]-oxadiazole

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Br:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17](=[N:19]O)[NH2:18]>>[Br:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]1[N:19]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:7][N:18]=1

Participants

Reactant 2

HCID 85014-Chlorobenzoyl chloride

HCID 865873543-Bromo-thiophene-2-amidoxime

Product 1

HCID 221479003-(3-Bromo-thiophen-2-yl)-5-(4-chloro-phenyl)-[1,2,4]-oxadiazole

Procedure

The title compound was prepared from 4-chloro-benzoyl chloride (60 μL, 0.47 mmol) and 3-bromo-thiophene-2-amidoxime (102 mg, 0.461 mmol) similar to Example 36c, and yielded 80 mg (51%) of white solid. 1H NMR (CDCl3): 8.15 (dd, J=9.09, 2.06 Hz, 2H), 7.54 (dd, J=8.51, 2.20 Hz, 2H), 7.50 (d, J=5.22 Hz, 1H), 7.18 (d, J=5.22 Hz, 1H).

Sources & evidence

ORD record: ord-e980165ce8d14c42ac2a291299a3bcc2
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041685B2

Reaction notes

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