Thionyl Chloride → HCID 178512519, compound

HRID 327869Notes

Reaction equation

HRID 327869 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3].S(Cl)([Cl:16])=O>>[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:16])=[O:10])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178512548HCID 178512548, compound

Product 1

HCID 178512519HCID 178512519, compound

Procedure

The antineoplastic drug shown as Compound 1 may be synthesized as follows: p-guanidinobenzoic acid is refluxed with thionyl chloride to yield the corresponding p-guanidinobenzoic acid chloride. This is then reacted with ethyl p-hydroxybenzoylacetate in the presence of a catalyst such as dimethylaminopyridine (DMAP) to yield Compound 2 of the following structure: ##STR12##

Workup

  1. custommay be synthesized

Sources & evidence

ORD record
ord-ae360254d4ed46a1b21b7b99ee3aacfc
Source dataset
uspto-grants-1993_12
Patent number
US05274162

Reaction notes

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