Triethylamine → 2,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanate

HRID 1768564

Reaktionsgleichung

Reaktionsgleichung von HRID 1768564
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](Cl)(Cl)=[S:20]>C1(C)C=CC=CC=1>[CH2:3]1[CH2:2][O:1][C:6]2[CH:7]=[CH:8][C:9]([N:11]=[C:19]=[S:20])=[CH:10][C:5]=2[O:4]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 891481,4-Benzodioxan-6-ylamine

Produkt 1

HCID 27761732,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanateAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 1,4-benzodioxan-6-amine (15.1 g; 100 mmol) and triethylamine (20.2 g; 200 mmol) in toluene (350 ml) was added dropwise over 10 min. thiophosgene (11.5 g; 100 mmol) in toluene (50 ml). The mixture was stirred at 80° C. for 30 min., cooled to room temperature and filtered. The filtrate was evaporated. The product was redissolved in toluene and concentrated in vacuo. The resulting oil was taken up in warm petroleum ether, which was filtered. The filtrate was concentrated to a small volume, which afforded 7.2 g of 3,4-ethylenedioxyphenylisothiocyanate.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionThe product was redissolved in toluene
  5. concentrationconcentrated in vacuo
  6. filtrationwhich was filtered
  7. concentrationThe filtrate was concentrated to a small volume, which

Quellen und Nachweise

ORD-Eintrag
ord-e8b66ff43a604f059838c162267d8a16
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05378714

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