Triethylamine → 5,6-Dihydro-3-hydroxy-2-phenylthiazolo-[2,3-a]isoquinolinium hydroxide

HRID 1109573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109573
[C:1]1(=[S:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.Br[CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](Cl)=[O:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH-:15].[OH:15][C:14]1[N+:2]2[CH2:3][CH2:4][C:5]3[C:10]([C:1]=2[S:11][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 598182Bromophenylacetyl chlorideHCID 28242121,2,3,4-Tetrahydroisoquinoline-1-thione

Produkt 1

HCID 190204015,6-Dihydro-3-hydroxy-2-phenylthiazolo-[2,3-a]isoquinolinium hydroxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

aa) Method A: 23.65 g of 3,4-dihydroisoquinoline-1(2H)-thione was dissolved in 750 ml of chloroform, whereupon the solution was treated at room temperature while cooling firstly with 54 g of α-bromophenylacetyl chloride and 90 minutes later with 53 ml of triethylamine and the mixture was stirred at room temperature overnight. The reaction mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. There was obtained 5,6-dihydro-3-hydroxy-2-phenylthiazolo[2,3-a]isoquinolinium hydroxide (internal salt) of m.p. 210° (dec.) (from acetonitrile/dioxane).

Aufarbeitung

  1. additionwas treated at room temperature
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0bbdb5a205e3479e81a78e37362a6ed8
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05321021

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