Diisopropylethylamine → 4-Nitrophenyl 1,1,1-trifluoro-2-methylpropan-2-ylcarbamate

HRID 589836

Reaktionsgleichung

Reaktionsgleichung von HRID 589836
[F:1][C:2]([F:8])([F:7])[C:3]([NH2:6])([CH3:5])[CH3:4].Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:11].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]([F:8])([F:7])[C:3]([NH:6][C:10](=[O:11])[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)([CH3:5])[CH3:4]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 112751881,1,1-Trifluoro-2-methylpropan-2-amine

Produkt 1

HCID 665841014-Nitrophenyl 1,1,1-trifluoro-2-methylpropan-2-ylcarbamateAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a solution of 0.35 g (2.75 mmol) of 1,1,1-trifluoro-2-methylpropan-2-ylamine (CAS 812-18-0) in 20 ml of dichloromethane, cooled to −15° C., is added dropwise 1.00 g (4.96 mmol) of 4-nitrophenyl chloroformate (CAS 7693-46-1) dissolved in 15 ml of dichloromethane, while maintaining the temperature at −15° C. 0.48 ml (2.75 mmol) of diisopropylethylamine in 10 ml of dichloromethane is then added, still at −15° C. Stirring is continued at −15° C. for 2 hours, and the temperature of the mixture is then allowed to return to 0° C. over 1 hour. 20 ml of saturated aqueous sodium hydrogen carbonate solution are then added. The organic phase is separated out by settling and dried over sodium sulfate, and the solvent is partially evaporated off under reduced pressure to a volume of about 8 ml. This solution is chromatographed on a column of 40 g of silica gel, eluting with a mixture of 20% cyclohexane in dichloromethane, to give 0.21 g of 4-nitrophenyl 1,1,1-trifluoro-2-methylpropan-2-ylcarbamate in the form of a white solid.

Aufarbeitung

  1. waitto return to 0° C. over 1 hour
  2. customThe organic phase is separated out
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is partially evaporated off under reduced pressure to a volume of about 8 ml
  5. customThis solution is chromatographed on a column of 40 g of silica gel
  6. washeluting with a mixture of 20% cyclohexane in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fc3b6c7a4e284c7db39ca0f8a09d666f
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233965B2

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