Triethylamine → N-(4-nitrophenoxycarbonyl)isopropoxylamine

HRID 1711150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711150
[CH:1]([O:4][NH2:5])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C(Cl)Cl.[Cl-].[Na+].O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][C:14]([NH:5][O:4][CH:1]([CH3:3])[CH3:2])=[O:15])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 2768923Hydroxylamine, O-(1-methylethyl)-

Produkt 1

HCID 86629518N-(4-nitrophenoxycarbonyl)isopropoxylamineAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To as solution of the crude O-isopropyl-hydroxylamine (200 mg) from above in CH2Cl2 (5 ml) was added Et3N (0.30 ml, 2.16 mmol) and 4-nitrophenyl chloroformate (430 mg, 2.13 mmol) and the mixture stirred at room temperature for 30 min. before diluting with CH2Cl2 (20 ml) and brine (15 ml). The aqueous layer was extracted with CH2Cl2 (1×15 ml) and the combined organic extracts dried (Na2SO4), concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 4:1) to afford N-(4-nitrophenoxycarbonyl)isopropoxylamine (290 mg) as a yellow oil.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with CH2Cl2 (1×15 ml)
  2. dry with materialthe combined organic extracts dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-d5fd77cbc51d4a8fb605dec382356b4f
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790747B2

Notizen zur Reaktion

Wird geladen…