Dichloromethane → Tienocarbine

HRID 647928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647928
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([CH3:12])[C:8]=2[CH:13]=1)N.C(Cl)Cl.[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.[OH-].[Na+]>O>[CH3:12][C:9]1[C:8]2=[C:13]3[C:4](=[CH:5][CH:6]=[C:7]2[S:11][CH:10]=1)[NH:2][C:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][C:20]3=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 204843225-Hydrazino-3-methylbenzothiophene hydrochloride

Produkt 1

HCID 71140Tienocarbine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

15,75 g of 5-hydrazino-3-methylbenzothiophene hydrochloride are suspended in 500 ml of water, a layer of methylene chloride is introduced under the suspension and 10.5 g of 1-methyl-4-piperidone are added at about 0° C. The mixture is then adjusted to pH 9.5 with N NaOH and is stirred for 30 minutes. The organic phase is separated off and washed with saturated NaCl solution, dried and mixed with 500 ml of ethylene glycol and the methylene chloride is distilled off under a vacuum of 12 mm. Some of the glycol is then distilled off under 0.01 mm and at 100° C. and the concentrated solution is heated to 200° C. (bath temperature) in an N2 atmosphere for 1/2 hour. The crystals which precipitate on cooling the mixture are filtered off, washed and recrystallised from ethyl acetate. Melting point: 224°-227° C.

Aufarbeitung

  1. additionare added at about 0° C
  2. customThe organic phase is separated off
  3. washwashed with saturated NaCl solution
  4. customdried
  5. additionmixed with 500 ml of ethylene glycol
  6. distillationthe methylene chloride is distilled off under a vacuum of 12 mm
  7. distillationSome of the glycol is then distilled off under 0.01 mm and at 100° C.
  8. customThe crystals which precipitate
  9. temperatureon cooling the mixture
  10. filtrationare filtered off
  11. washwashed
  12. customrecrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2b59b9bdaff6450eba2b60dd4df3d5a4
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410536

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