5-Formyl-2-thiophenecarboxylic Acid → 5-[3-(4-Hydroxy-3,5-dimethyl-phenyl)-[1,2,4]oxadiazol-5-yl]-thiophene-2-carbaldehyde

HRID 1685735Notes

Reaction equation

HRID 1685735 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1)=[O:2].[OH:11][C:12]1[C:21]([CH3:22])=[CH:20][C:15]([C:16]([NH:18]O)=[NH:17])=[CH:14][C:13]=1[CH3:23]>>[OH:11][C:12]1[C:13]([CH3:23])=[CH:14][C:15]([C:16]2[N:17]=[C:8]([C:6]3[S:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=3)[O:10][N:18]=2)=[CH:20][C:21]=1[CH3:22]

Participants

3

Reactant 2

HCID 8188825-Formyl-2-thiophenecarboxylic AcidHCID 178426654HCID 178426654, compound

Product 1

HCID 1363773255-[3-(4-Hydroxy-3,5-dimethyl-phenyl)-[1,2,4]oxadiazol-5-yl]-thiophene-2-carbaldehydeYield 15.5%

Procedure

The title compound (140 mg) is prepared from 5-formyl-2-thiophene carboxylic acid (468 mg, 3.0 mmol) and 4,N-dihydroxy-3,5-dimethyl-benzamidine (540 mg, 3.0 mmol) according to Method A; LC-MS: tR=1.01 min; [M+1]+=301.04; 1H NMR (D6-DMSO): δ2.24 (s, 6H), 7.64 (s, 2H), 8.17 (s, 2H), 8.99 (s, 1H), 10.06 (s, 1H).

Sources & evidence

ORD record
ord-fb5ecfa57f3448129744e995582fe621
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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