Hydrochloric Acid → Ethyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate

HRID 62679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62679
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)OC(C)(C)C)=[C:8]([NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[CH:7]=1.Cl>CO.O1CCOCC1>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][C:8]=1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 71007309Tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate

Produkt 1

HCID 86712524Ethyl (2-amino-5-(thiophen-2-yl)phenyl)carbamateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate (0.10 g, 0.28 mmol, 1.0 equiv.) in MeOH (2 mL) at 0° C. was added a 4M solution of HCl in dioxane (1.5 mL). The reaction was warmed to room temperature and stirred for 2 h, The reaction was concentrated under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added. The obtained solid was filtered, washed with water and dried. The crude material was purified by column chromatography (silica gel, 15% EtOAc/hexanes) to give ethyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate (0.05 g, 69% yield).

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionA saturated aqueous solution of sodium bicarbonate was added
  3. filtrationThe obtained solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude material was purified by column chromatography (silica gel, 15% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7e13d12884744bc8a59977d3e9b152f1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447030B2

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