Triethylamine → 5-Isothiocyanato-2-(thiophen-2-yl)-1,3-benzothiazole

HRID 1287837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287837
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[N:7][C:6]=2[CH:15]=1.C(N(CC)CC)C.[C:23](Cl)(Cl)=[S:24]>O1CCCC1>[N:1]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[N:7][C:6]=2[CH:15]=1)=[C:23]=[S:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 215066992-(Thiophen-2-yl)-1,3-benzothiazol-5-amine

Produkt 1

HCID 127819415-Isothiocyanato-2-(thiophen-2-yl)-1,3-benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Amino-2-(2-thienyl)benzothiazole 7.0 g, 0.03 M is dissolved in 400 cc of tetrahydrofuran and 8.4 cc, 0.06 M, of triethylamine. Thiophosgene 2.3 cc, 0.03 M, is added, and the resulting mixture stirred at ambient temperature overnight. The solids which form are filtered, and washed with tetrahydrofuran. The filtrate is concentrated to dryness, and chromatographed on Alumina IV. The product is recrystallized from acetonitrile to yield 5.7 g of colorless needles, 70% of theory, m.p. 147°-149°.

Aufarbeitung

  1. filtrationThe solids which form are filtered
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated to dryness
  4. customchromatographed on Alumina IV
  5. customThe product is recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-67a8f48d06794da59e54157f6e05fde4
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03985885

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