4-chloro-N'-hydroxybenzenecarboximidamide → 5-(3-Bromo-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]oxadiazole

HRID 1823874Notes

Reaction equation

HRID 1823874 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:17]=[CH:16][O:15][C:14]=1[C:18](Cl)=O>>[Br:12][C:13]1[CH:17]=[CH:16][O:15][C:14]=1[C:18]1[O:9][N:8]=[C:6]([C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:7]=1

Participants

3

Reactant 2

HCID 2246504-chloro-N'-hydroxybenzenecarboximidamideHCID 218645763-Bromofuran-2-carbonyl chloride

Product 1

HCID 98584885-(3-Bromo-furan-2-yl)-3-(4-chloro-phenyl)-[1,2,4]oxadiazole

Procedure

The title compound was prepared from 4-chlorobenzamidoxime (479 mg, 2.29 mmol) and 3-bromo-furan-2-carbonyl chloride (390 mg, 2.29 mmol) similar to Example 16, and yielded 570 mg (81%) of white solid. 1H NMR (CDCl3): 8.13 (dd, J=8.80, 2.20 Hz, 2H), 7.67 (d, J=1.92 Hz, 1H), 7.49 (dd, J=8.79, 2.20 Hz, 2H), 6.75 (d, J=1.92 Hz, 1H).

Sources & evidence

ORD record
ord-209694eaeb0a4a70b88b83c6f9d24fb5
Source dataset
uspto-grants-2006_05
Patent number
US07041685B2

Reaction notes

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