Thionyl Chloride → HCID 56629765, Verbindung

HRID 127578

Reaktionsgleichung

Reaktionsgleichung von HRID 127578
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[NH:3]1.[C:16]([S:24][CH2:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(SCC(C)C(O)=O)(=O)C1C=CC=CC=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:16]([S:24][CH2:25][CH:26]([CH3:30])[C:27]([N:3]1[C@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 24386Thionyl ChlorideHCID 5694973-(Benzoylthio)-2-methylpropanoic acidHCID 2760578methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochlorideHCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioate

Produkt 1

HCID 56629765HCID 56629765, VerbindungAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

5.69 g of methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride are suspended in 50 ml of chloroform, and 5.6 g of triethylamine are added thereto under ice-cooling and stirring. 3-benzoylthio-2-methylpropionyl chloride (which is prepared by heating a mixture of 5.6 g of 3-benzoylthio-2-methyl-propionic acid and 6 ml of thionyl chloride at 60° C. for 2 hours, followed by distillation thereof to remove the excess of thionyl chloride) is dissolved in 10 ml of tetrahydrofuran, and said tetrahydrofuran solution is added dropwise to the suspension obtained above. After the mixture is stirred at room temperature overnight, the chloroform layer is collected therefrom and washed with water, an aqueous sodium bicarbonate solution, diluted hydrochloric acid and water, successively. The chloroform solution is dried and then distilled to remove solvent. The residue thus obtained is purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1)). 8.0 g of methyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate are obtained as colorless oil. Yield: 80.5 %

Aufarbeitung

  1. temperatureunder ice-cooling
  2. temperatureby heating
  3. distillationfollowed by distillation
  4. customto remove the excess of thionyl chloride)
  5. dissolutionis dissolved in 10 ml of tetrahydrofuran
  6. additionis added dropwise to the suspension
  7. customobtained above
  8. stirringAfter the mixture is stirred at room temperature overnight
  9. customthe chloroform layer is collected
  10. washwashed with water
  11. dry with materialThe chloroform solution is dried
  12. distillationdistilled
  13. customto remove solvent
  14. customThe residue thus obtained
  15. customis purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1))

Quellen und Nachweise

ORD-Eintrag
ord-2813aaff273042e3820a4bb2b0273ddf
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256751

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