Diisopropylethylamine → 4-Nitrophenyl 4,4,4-trifluorobutylcarbamate

HRID 589830

Reaktionsgleichung

Reaktionsgleichung von HRID 589830
[F:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][CH2:5][NH2:6].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])[CH2:3][CH2:4][CH2:5][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

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 1366454,4,4-TrifluorobutylamineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 665841404-Nitrophenyl 4,4,4-trifluorobutylcarbamateAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a solution of 0.35 g (2.75 mmol) of 4,4,4-trifluoro-butylamine (CAS 819-46-5) 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 still at −15° C. is then added. Stirring is continued at −15° C. for 45 minutes, and the temperature of the mixture is then allowed to return to 0° C. over 30 minutes. 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 0.76 g of 4-nitrophenyl 4,4,4-trifluorobutylcarbamate in the form of a white solid.

Aufarbeitung

  1. waitto return to 0° C. over 30 minutes
  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-bee3a2e119ef41469fffe701f59b535f
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233965B2

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