Triethylamine → N-(2-hydroxy-4-nitrophenyl)-N'-(2,3-methylenedioxyphenyl)urea

HRID 568000

Reaktionsgleichung

[CH2:1]1[O:9][C:8]2[C:3](=[C:4](C(O)=O)[CH:5]=[CH:6][CH:7]=2)[O:2]1.C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][C:39]=1[OH:47]>C1(C)C=CC=CC=1>[OH:47][C:39]1[CH:40]=[C:41]([N+:44]([O-:46])=[O:45])[CH:42]=[CH:43][C:38]=1[NH:37][C:18]([NH:15][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)=[O:27]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of the 2,3-methylenedioxyphenylcarboxylic acid in toluene, triethylamine (0.27 mL, 1.95 mmol) and diphenylphosphoryl azide (DPPA) (0.32 mL, 1.5 mmol) were added. The reaction mixture was stirred at 60° C. for 2 hours, then 2-amino-5-nitrophenol (250 mg, 1.5 mmol) was added. The reaction mixture was stirred at 100° C. for 18 hours. After the reaction mixture was cooled to room temperature, it was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. Chromatography of the resulting solid on silica gel (hexane:ethyl acetate; 5:1) gave product (200 mg, 42%). EI-MS m/z 318 (M+H)+.

Aufarbeitung

stirringThe reaction mixture was stirred at 100° C. for 18 hours
temperatureAfter the reaction mixture was cooled to room temperature
customit was partitioned between 5% citric acid and ethyl acetate
customThe organic layer was separated
extractionthe aqueous layer was extracted three times with ethyl acetate
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-96cb9ac5b435487893ff6a2492c89b0f
Quelldatensatz: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06180675B2

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