Water → HCID 90224812, compound

HRID 1487099Notes

Reaction equation

[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[C:12](=N)[NH:11][C:10]2=[O:19])=[CH:4][C:3]=1[CH3:20].O.C(=O)([O-])[OH:23].[Na+]>C(O)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[C:12](=[O:23])[NH:11][C:10]2=[O:19])=[CH:4][C:3]=1[CH3:20]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-(4-bromo-3,5-dimethylphenyl)-4-imino-1,3-diazaspiro[4.4]nonan-2-one (the crude product obtained in the previous reaction) in acetic acid (1.0 mL) and water (0.25 mL) was stirred for 1.5 hours at 65° C. under nitrogen atmosphere. After further addition of acetic acid (1.0 mL) and water (0.25 mL), the mixture was stirred for 17 hours at 65° C. under nitrogen atmosphere. The reaction mixture was cooled, followed by dilution with water and adjustment of its pH to 8 using a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane) to afford 1-(4-bromo-3,5-dimethylphenyl)-1,3-diazaspiro[4.4]nonane-2,4-dione (121 mg).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record: ord-09a23fa46c294ed3849ce6404d261c8c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428505B2

Reaction notes

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