Triethylamine → Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

HRID 1076834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076834
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[SH:18].[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]=[C:34]=S)=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:11]2[S:18][C:34]([NH:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:28][CH:29]=3)=[N:9][C:10]=2[CH:15]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidineHCID 121992962-Amino-4-methoxybenzene-1-thiol hydrochloride

Produkt 1

HCID 38054Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triethylamine (0.7 ml.) is added to a suspension of 2-amino-4-methoxybenzenethiol hydrochloride (0.96 g.) in toluene (20 ml.) under nitrogen. 4-(2-Pyrrolidin-1-ylethoxy)phenyl isothiocyanate (1.24 g.) is added and the mixture stirred and heated under reflux for 16 hours. Ethyl acetate and 10% sodium hydroxide are added and the organic layer separated, washed with water and dried. The organic layer is passed through a column of silica gel (2 × 20 cm.) and the filtrate rejected. The column is eluted with methanol, which, on concentration gives 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole, m.p. 167° - 168°C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. customthe organic layer separated
  4. washwashed with water
  5. customdried
  6. washThe column is eluted with methanol, which, on concentration

Quellen und Nachweise

ORD-Eintrag
ord-8212335d39954d859208caa13f472fa5
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03957999

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