2-Nitrobenzyl alcohol → o-Nitrobenzyl benzylcarbamate

HRID 399372

Reaktionsgleichung

Reaktionsgleichung von HRID 399372
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[CH2:12]([N:19]=[C:20]=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:12]([NH:19][C:20](=[O:21])[O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 119232-Nitrobenzyl alcoholHCID 76639Benzyl isocyanate

Produkt 1

HCID 54357994o-Nitrobenzyl benzylcarbamateAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

10 ml of toluene, 5.75 g of 2-nitrobenzyl alcohol and 5 g of benzyl isocyanate were heated to reflux for 3 hours in a nitrogen atmosphere. Following cooling of the mixture, 50 ml of toluene was added. This reaction solution was washed several times with water, and was then dehydrated with sodium sulfate. The sodium sulfate was then filtered out, and the solvent was removed from the filtrate by means of a rotary evaporator. The solid obtained was recrystallized from a hexane-toluene mixed solvent, producing 7.3 g of o-nitrobenzyl benzylcarbamate in the form of plate yellow crystals. This compound had a melting point of 110° to 111° C., and the infrared absorption spectrum was 3308 cm-1 : N--H, 1696 cm-1 : C=O, 1520 cm-1 : N--O.

Aufarbeitung

  1. temperatureto reflux for 3 hours in a nitrogen atmosphere
  2. additionwas added
  3. washThis reaction solution was washed several times with water
  4. filtrationThe sodium sulfate was then filtered out
  5. customthe solvent was removed from the filtrate by means of a rotary evaporator
  6. customThe solid obtained
  7. customwas recrystallized from a hexane-toluene mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-3298aea7a9fa46d480cf89f625cec7f6
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05820944

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