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

HRID 568000
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 568000
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3048321,3-Dioxaindane-4-carboxylic acidHCID 49847212-Amino-5-Nitrophenol

Produkt 1

HCID 9883432N-(2-hydroxy-4-nitrophenyl)-N'-(2,3-methylenedioxyphenyl)ureaAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

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

  1. stirringThe reaction mixture was stirred at 100° C. for 18 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customit was partitioned between 5% citric acid and ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. 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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