Cyanamide → N-cyano-3-chloro-thiophene-2-carboxylic acid amide

HRID 2114910Notes

Reaction equation

HRID 2114910 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].[N:10]#[C:11][NH2:12]>>[C:11]([NH:12][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[Cl:1])=[O:8])#[N:10]

Participants

3

Reactant 2

HCID 9864CyanamideHCID 27358243-Chlorothiophene-2-carbonyl chloride

Product 1

HCID 23570762N-cyano-3-chloro-thiophene-2-carboxylic acid amide

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.

Workup

  1. customCompounds of this invention with a linker between middle ring and Ar2 may be prepared
  2. customas illustrated by the exemplary reaction in Scheme 11

Sources & evidence

ORD record
ord-8af6eca9d96045a4941a7ca484336759
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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