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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 489234Generated: October 30, 2026

TFA dichloromethane water → 6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2-thioxo-1,3-diazaspiro[4.4]nonan-4-one

https://huagongshe.com/reaction/489234

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTFA dichloromethane waterHCID 18672661—
Reactant6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl esterHCID 23588562—
Product6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2-thioxo-1,3-diazaspiro[4.4]nonan-4-oneHCID 2202528860.4%

Reaction Steps

6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (42 mg, 74 μmol) (Preparation 10) was added to a TFA/DCM/H2O (1/1/0.1) solution (1 ml) at RT. After 30 min the reaction mixture was concentrated to give a beige solid which was washed with pentane to yield 6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2-thioxo-1,3-diazaspiro[4.4]nonan-4-one (21 mg, beige solid). 1H NMR (CDCl3): 8.39 (1H, s), 7.51 (2H, d, J=8.4 Hz), 7.35 (1H, m), 7.19 (2H, d, J=8.4 Hz), 6.44 (2H, m), 3.36 (1 H, dd, J1=12.9 Hz, J2=6.1 Hz), 2.45-2.65 (2H, m), 1.8-2.25 (4H, m).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06977267B2
Source datasetuspto-grants-2005_12
ORD IDord-391d1df744114136a458eae9aa7689be
Source noteuspto-grants-2005_12