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

HRID 1076832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076832
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]Cl)=[CH:14][CH:13]=3)=[N:8][C:7]=2[CH:22]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>COCCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:14][CH:13]=3)=[N:8][C:7]=2[CH:22]=1

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 215385995-Methoxy-2-[4-(2-chloroethoxy)anilino]benzothiazole

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-methoxy-2-[4-(2-chloroethoxy)anilino]benzothiazole (200 g.), pyrrolidine (144 ml.) and 2-methoxyethanol (1 liter) is boiled under reflux for 16 hours. The mixture is evaporated from the steam bath at reduced pressure and the residue dissolved in approximately 2N hydrochloric acid. The solution is washed with ethyl acetate, basified with 40% sodium hydroxide solution and extracted with chloroform. The chloroform is washed with water, dried over magnesium sulphate and passed through a column of alumina. The column is washed with chloroform and the combined chloroform solutions evaporated. The residue is recrystallised from 2-methoxyethanol to give 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole, m.p. 167° - 168°C.

Aufarbeitung

  1. temperatureunder reflux for 16 hours
  2. customThe mixture is evaporated from the steam bath at reduced pressure
  3. dissolutionthe residue dissolved in approximately 2N hydrochloric acid
  4. washThe solution is washed with ethyl acetate
  5. extractionextracted with chloroform
  6. washThe chloroform is washed with water
  7. dry with materialdried over magnesium sulphate
  8. washThe column is washed with chloroform
  9. customthe combined chloroform solutions evaporated
  10. customThe residue is recrystallised from 2-methoxyethanol

Quellen und Nachweise

ORD-Eintrag
ord-7b807eee5d1a450c9885bdbf191aba69
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03957999

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