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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1468233Generated: October 31, 2026

2-Oxopropanethioamide → 7'-Bromo-4-methoxy-5''-methyl-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thione

https://huagongshe.com/reaction/1468233

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-OxopropanethioamideHCID 20765237—
Reactant7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imineHCID 86706709—
SolventMethanolHCID 887—
Product7'-Bromo-4-methoxy-5''-methyl-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thioneHCID 8670671043.2%

Reaction Conditions

Temperature60 °C

Reaction Steps

7′-Bromo-4-methoxy-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-naphthalen]-1′-imine (Intermediate 14, 0.350 g, 1.09 mmol) and 2-oxopropanethioamide (Intermediate 1, 0.336 g, 3.26 mmol) were dissolved in dry MeOH (5 mL) and the resulting orange solution was heated at 60° C. under N2 (g) overnight. The mixture was concentrated and purified by flash column chromatography using a gradient of 0-10% EtOAc in heptane to give the title compound (0.192 g, 43% yield): MS (ES+) m/z 407.12 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09000184B2
Source datasetuspto-grants-2015_04
ORD IDord-201087d91b4241139b27c8aec8d5d189
Source noteuspto-grants-2015_04