4-Chlorobenzaldehyde → (4-Chloro-benzylidene)-[5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-amine

HRID 2114911Notes

Reaction equation

HRID 2114911 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[Cl:12])[O:4][N:3]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[N:1][C:2]2[N:6]=[C:5]([C:7]3[S:8][CH:9]=[CH:10][C:11]=3[Cl:12])[O:4][N:3]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 221478623-Amino-5-(3-chloro-2-thienyl)-1,2,4-oxadiazole

Product 1

HCID 69088885(4-Chloro-benzylidene)-[5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compounds of this invention with a linker between middle ring and Ar2 may be prepared as illustrated by the exemplary reaction in Scheme 11. Reaction of 3-chloro-thiophene-2-carbonyl chloride with cyanamide produces N-cyano-3-chloro-thiophene-2-carboxylic acid amide, followed by treating with hydroxyamine to give 3-amino-5-(3-chloro-2-thienyl)-1,2,4-oxadiazole. The amine was refluxed with 4-chlorobenzaldehyde in toluene to produce (4-chloro-benzylidene)-[5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-amine.

Sources & evidence

ORD record
ord-4c849772ed004dd096509f80d6bf1840
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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