Thiophosgene → N-chlorothiocarbonyl-2-ethoxycarbonylhexahydropyridine

HRID 1995850Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].[C:12](Cl)([Cl:14])=[S:13]>>[Cl:14][C:12]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[S:13]

Participants

Reactant 2

HCID 10040Thiophosgene

HCID 27517Ethyl piperidine-2-carboxylate

Product 1

HCID 53829765N-chlorothiocarbonyl-2-ethoxycarbonylhexahydropyridine

Procedure

In the same way, 3-[2-(4-chlorobenzyloxy)-5-pyridyl]-1,5-tetramethylene-4-thiohydantoin is prepared by reacting 2-ethoxycarbonylhexahydropyridine with thiophosgene to give N-chlorothiocarbonyl-2-ethoxycarbonylhexahydropyridine, which is then reacted with 2-(4-chlorobenzyloxy)-5-aminopyridine.

Sources & evidence

ORD record: ord-60bd5108cf4c4d6f892f2d6c009bd372
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04406689

Reaction notes

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