Ethyl chloroformate → Ethyl (2-(thiophen-3-yl)ethyl)carbamate

HRID 423381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423381
C(N(C(C)C)CC)(C)C.Cl.[S:11]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12]1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>ClCCl>[CH2:23]([O:22][C:20](=[O:21])[NH:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][S:11][CH:12]=1)[CH3:24]

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 122587382-(Thiophen-3-yl)ethan-1-amine hydrochloride

Produkt 1

HCID 49670241Ethyl (2-(thiophen-3-yl)ethyl)carbamateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add diisopropylethylamine (54.0 g, 418.0 mmol) to a suspension of 2-thiophene-3-yl-ethylamine hydrochloride in dichloromethane (400 mL) and stir the mixture for 40 min at RT. Cool the mixture to 0° C. and add dropwise ethyl chloroformate (22.7 g, 209.0 mmol) over 15 min. After the addition is complete, stir the reaction for 1 h at 0° C. Wash with 10% sodium bisulfate (500 mL). Extract the aqueous portion with dichloromethane (2×100 mL) and dry the combined organic portions over Na2SO4, filter and concentrate in vacuo. Purify the resulting residue by silica gel chromatography, using an eluent of 100% dichloromethane to give 22.6 g (60%) of the title compound. MS/ES m/z 200.3 [M+H]+.

Aufarbeitung

  1. temperatureCool the mixture to 0° C.
  2. additionAfter the addition
  3. stirringstir
  4. customthe reaction for 1 h at 0° C
  5. washWash with 10% sodium bisulfate (500 mL)
  6. extractionExtract the aqueous portion with dichloromethane (2×100 mL)
  7. dry with materialdry the combined organic portions over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify the resulting residue by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1cb98613bd774e7c9325d279791b2285
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101764B2

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