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

HRID 2114926Notes

Reaction equation

HRID 2114926 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[N:9]O)[NH2:8].Br[C:12]1[CH:16]=[CH:15]S[C:13]=1[C:17]#N.[ClH:19].NO.[CH2:22]([OH:24])[CH3:23]>>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[N:9]=[C:22]([C:23]2[CH:15]=[CH:16][C:12]([Cl:19])=[CH:13][CH:17]=2)[O:24][N:8]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 27400883-Bromothiophene-2-carbonitrileHCID 865873543-Bromo-thiophene-2-amidoxime

Product 1

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

Procedure

3-Bromo-thiophene-2-amidoxime: The title compound was prepared from 3-bromo-2-cyano-thiophene (564 mg, 3.00 mmol) and 0.576 M hydroxylamine hydrochloride in 95% ethanol (5.8 μL, 3.3 mmol) similar to Example 36c, and yielded 383 mg (58%) of white solid. 1H NMR (Acetone-d6): 9.18 (s, 1H), 7.51 (d, J=5.50 Hz, 1H), 7.06 (d, J=5.22 Hz, 1H), 5.59 (s, 2H).

Sources & evidence

ORD record
ord-ad77e520536c4c3e90bbd98c68b668c8
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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