Imolamine

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Imolamine (INN, BAN; brand names Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax) is a coronary vasodilator which is used in the treatment of angina pectoris and as a local anesthetic.[1][2]

Use patents:[3][4]

Synthesis

Butalamine has very similar synthesis but is alkylated on the alternate nitrogen position.

File:Imolamine synthesis.svg
Thieme Patent[5]

The reaction of benzoylchloride oxime [698-16-8] (2) with Cyanamide (3) gives 3-Phenyl-1,2,4-oxadiazol-5-amine [3663-37-4] (4). Alkylation with 2-chlorotriethylamine [100-35-6] (5) in the presence of KOH base occurs at the endocyclic ring nitrogen completing the synthesis of imolamine (6).

EFforts towards Onepot method (section 2.5 & 2.6).

References

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  3. Anne Rolland, <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1986 to Laboratoires Albert Rolland SA).
  4. Anne Rolland, <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1986 to Laboratoires Albert Rolland SA).
  5. FR2023M idem J M D Aron-Samuel & J J Sterne, <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1965-11-17).

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