Cyanamide → 27314-97-2

HRID 967291Notes

Reaction equation

[CH:1]1[CH:9]=[CH:8][C:7]2[C:3](=[N:4][O:5][N+:6]=2[O-:10])[CH:2]=1.[N:11]#[C:12][NH2:13]>>[CH:1]1[CH:9]=[CH:8][C:7]2[N+:6]([O-:10])=[N:11][C:12]([NH2:13])=[N+:4]([O-:5])[C:3]=2[CH:2]=1

Participants

Reactant 2

HCID 9864Cyanamide

HCID 68075Benzofuroxan

Product 1

HCID 13541351127314-97-2

Procedure

More particularly, benzofuroxan is reacted with a stoichiometric excess of cyanamide in the presence of an organic base in a non-aqueous medium at about room temperature. When the reaction is complete the reaction mixture is treated with an organic acid to give tirapazamine.

Workup

additionis treated with an organic acid

Sources & evidence

ORD record: ord-4de511242ae242cc8d37cf0bac72b8d1
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953852B2

Reaction notes

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