Dimethylamine → 8-Chloro-2-[2-(dimethylamino)ethyl]-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione hydrochloride

HRID 1194221

Reaktionsgleichung

Reaktionsgleichung von HRID 1194221
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[S:15])[N:7]([CH3:14])[CH2:8][CH:9]([CH2:11][CH2:12]Cl)[O:10][C:4]=2[CH:3]=1.[CH3:18][NH:19][CH3:20]>C(O)C.Cl>[ClH:1].[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[S:15])[N:7]([CH3:14])[CH2:8][CH:9]([CH2:11][CH2:12][N:19]([CH3:20])[CH3:18])[O:10][C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 674DimethylamineHCID 137262998-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione

Produkt 1

HCID 137263298-Chloro-2-[2-(dimethylamino)ethyl]-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 9.8 g (0.04 mole) of 8-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione in 50 ml of absolute ethanol and 10 ml of a 40% aqueous solution of dimethylamine were mixed and heated in a steel bomb at 100° C. for 16 hr. The ethanol was evaporated under reduced pressure and the residue dissolved in chloroform and partitioned with 10% sodium hydroxide solution. The chloroform layer was evaporated under reduced pressure to give an amorphous solid. The solid was dissolved in 6N hydrochloric acid and the solution washed with ethyl acetate. The aqueous layer was basified with 50% sodium hydroxide and extracted with ethyl acetate. The ethyl acetate layer was evaporated under reduced pressure to give a viscous oil comprised substantially of the free base of the title compound which was dissolved in absolute ethanol and reacted with ethereal hydrogen chloride. The hydrochloride salt was recrystallized from ethanol to give 30 g (25%) product, m.p. 196°-199° C.

Aufarbeitung

  1. customThe ethanol was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in chloroform
  3. custompartitioned with 10% sodium hydroxide solution
  4. customThe chloroform layer was evaporated under reduced pressure
  5. customto give an amorphous solid
  6. washthe solution washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. customThe ethyl acetate layer was evaporated under reduced pressure
  9. customto give a viscous oil

Quellen und Nachweise

ORD-Eintrag
ord-c89da741a9c340f0aa96b92c8044e33b
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04812565

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