Methyl Ethyl Ketone → 1,5,5-trimethyl-3-[4-[2-oxo-8-propyl-4-(trifluoromethyl)-2H-chromen-7-yloxy]butyl]imidazolidine-2,4-dione

HRID 2074434

Reaction equation

CC(=O)CC.[OH:6][C:7]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]2[C:10]([C:11]([C:21]([F:24])([F:23])[F:22])=[CH:12][C:13](=[O:20])[O:14]2)=[CH:9][CH:8]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]([CH3:37])([CH3:36])[N:32]([CH3:38])[C:31]1=[O:39].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:38][N:32]1[C:33]([CH3:37])([CH3:36])[C:34](=[O:35])[N:30]([CH2:29][CH2:28][CH2:27][CH2:26][O:6][C:7]2[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]3[C:10]([C:11]([C:21]([F:24])([F:22])[F:23])=[CH:12][C:13](=[O:20])[O:14]3)=[CH:9][CH:8]=2)[C:31]1=[O:39]

Participants

Conditions

Temperature: 80 °C

Procedure

A 2-butanone (2 mL) solution of 7-hydroxy-8-propyl-4-(trifluoromethyl)-2H-chromen-2-one (30 mg, 0.11 mmol), 3-(4-bromobutyl)-1,5,5-trimethylimidazolidine-2,4-dione (30.5 mg, 0.11 mmol), and potassium carbonate (22.8 mg, 0.165 mmol) was heated and stirred overnight at 80° C. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated under vacuum. The obtained residue was purified using thin-layer silica-gel chromatography (hexane:ethyl acetate=1:1), and 53.5 mg of the title compound (yield 100%) was obtained as colorless oil.

Workup

extractionextracted with ethyl acetate
washSubsequently, the organic layer was washed with saturated saline
customdried
concentrationconcentrated under vacuum
customThe obtained residue was purified

Sources & evidence

ORD record: ord-2a4c7284e12349bbb711d1dab2d8dd90
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919509B2

Linked notes

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