3,5-Dinitroaniline → 1-(3,5-Dinitrophenyl)pyrrole

HRID 64106

Reaktionsgleichung

Reaktionsgleichung von HRID 64106
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[CH:16]=[CH:20][CH:19]=[CH:18]2)[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 120683,5-DinitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Produkt 1

HCID 173821411-(3,5-Dinitrophenyl)pyrroleAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 3,5-dinitroaniline (10 g, 54.644 mmol) and 2,5-dimethoxytetrahydrofuran (18.05 g, 136.61 mmol, 2.5 eq.) in acetic acid (122 ml) was heated to 100° C. for 16 h. Completion of reaction was monitored by TLC. Then the mixture was brought to RT and poured into ice-cold water. The precipitate was filtered, washed with water (150 ml) and dried to give the product in 54% yield (8.2 g). LC-MS (ESI): Calculated mass: 233.18; Observed mass: 233.04 [M+H]+ (rt: 1.667 min).

Aufarbeitung

  1. customCompletion of reaction
  2. customwas brought to RT
  3. additionpoured into ice-cold water
  4. filtrationThe precipitate was filtered
  5. washwashed with water (150 ml)
  6. customdried
  7. customto give the product in 54% yield (8.2 g)
  8. custom233.04 [M+H]+ (rt: 1.667 min)

Quellen und Nachweise

ORD-Eintrag
ord-e64e373a2f2e47dbaca16cc4542900eb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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