Dimethylformamide → 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methyl-3-[4-[2-oxo-8-propyl-4-(trifluoromethyl)-2H-chromen-7-yloxy]butyl]imidazolidine-2,4-dione

HRID 2074433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2074433
CN(C)C=O.Br[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:21]([CH2:22][CH2:23][CH3:24])=[C:20]2[C:15]([C:16]([C:26]([F:29])([F:28])[F:27])=[CH:17][C:18](=[O:25])[O:19]2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[O:36]1[CH2:41][CH2:40][O:39][C:38]2[CH:42]=[C:43]([C:46]3([CH3:53])[NH:50][C:49](=[O:51])[NH:48][C:47]3=[O:52])[CH:44]=[CH:45][C:37]1=2>O>[O:36]1[CH2:41][CH2:40][O:39][C:38]2[CH:42]=[C:43]([C:46]3([CH3:53])[NH:50][C:49](=[O:51])[N:48]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]4[C:21]([CH2:22][CH2:23][CH3:24])=[C:20]5[C:15]([C:16]([C:26]([F:29])([F:28])[F:27])=[CH:17][C:18](=[O:25])[O:19]5)=[CH:14][CH:13]=4)[C:47]3=[O:52])[CH:44]=[CH:45][C:37]1=2

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 32951335-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-methylimidazolidine-2,4-dioneHCID 579630147-(4-bromobutoxy)-8-propyl-4-(trifluoromethyl)-2H-chromen-2-one

Produkt 1

HCID 441875605-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methyl-3-[4-[2-oxo-8-propyl-4-(trifluoromethyl)-2H-chromen-7-yloxy]butyl]imidazolidine-2,4-dioneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

An N,N-dimethylformamide (2 mL) solution of 7-(4-bromobutoxy)-8-propyl-4-(trifluoromethyl)-2H-chromen-2-one (30 mg, 0.074 mmol) was added with potassium carbonate (20.4 mg, 0.148 mmol) and 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methylimidazolidine-2,4-dione (27.4 mg, 0.111 mmol) and then stirred overnight. 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=5:2), and the title compound (40.2 mg, 95%) was obtained as colorless oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe obtained residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-5de2f72c0bd34b2682f13e413149d14f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919509B2

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