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Triethylamine → 1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol

HRID 2258111
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2258111
Cl.[OH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.Cl[CH2:15][CH2:16][N:17]=[C:18]=[S:19]>ClCCl>[OH:2][CH:3]1[CH2:6][N:5]([C:18]2[S:19][CH2:15][CH2:16][N:17]=2)[CH2:4]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1386612-Chloroethyl IsothiocyanateHCID 27592903-Hydroxyazetidine hydrochloride

Produkt 1

HCID 109865151-(4,5-Dihydrothiazol-2-yl)azetidin-3-olAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 1.5 ml solution of acetonitrile anhydride containing 219 mg of 3-hydroxyazetidine hydrochloride (5) was cooled to 0° C. in the stream of nitrogen, and, to this solution, there were added 0.31 ml of triethylamine and subsequently a 0.3 ml solution of acetonitrile anhydride containing 250 mg of chloroethylisothiocyanate dissolved therein, and the resultant solution was stirred for 30 minutes at the same temperature, and, after left still until it had a room temperature, the solution was further stirred for two hours. Next, dichloromethane was added to the reaction liquid, and the resultant solution was washed with a saturated aqueous solution of potassium carbonate, and, thereafter, the dichloromethane layer was dried with magnesium sulfate, and then was condensed under reduced pressure, and, thus, there was obtained 300 mg (yield: 95%) of 3-hydroxy-1-(1,3-thiazolin-2-yl)azetidine (6) in the form of colorless needle crystal.

Aufarbeitung

  1. waitafter left still until it
  2. customhad a room temperature
  3. washthe resultant solution was washed with a saturated aqueous solution of potassium carbonate
  4. dry with materialthe dichloromethane layer was dried with magnesium sulfate
  5. customcondensed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-17388289ff4a47e8b6d01620f67d7b04
Quelldatensatz
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05659043

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