Dimethyl Disulfide → 1-methylthiomethyl-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

HRID 46520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46520
C([Li])CCC.[CH3:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12.[CH3:25][S:26]SC>CCCCCC.O1CCCC1>[CH3:25][S:26][CH2:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12

Komponenten

6

Edukt 3

HCID 12232Dimethyl DisulfideHCID 205556141-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2oneHCID 178418339Butyllithium

Produkt 1

HCID 205555951-methylthiomethyl-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

The starting material is prepared as follows: 36.4 ml of 2.5 M n-butyl lithium in hexane are added dropwise under nitrogen and at room temperature to the stirred suspension of 7.8 g of 1-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]-azepin-2-one in 70 ml of anhydrous tetrahydrofuran. The mixture is stirred at room temperature for 45 minutes and cooled in a dry ice-acetone bath. The solution of 5.45 ml of dimethyl disulfide in 60 ml of tetrahydrofuran is added dropwise and the mixture stirred with said cooling for 2 hours. It is quenched by the slow addition of 150 ml of water, the mixture is extracted with chloroform, the extract is dried and evaporated. The residue is crystallized from diethyl ether and recrystallized from ethyl acetate, to give the 1-methylthiomethyl-3,4,5,5a,6,7-hexahydro9-methoxy-2H-naphth[1,2-d]azepin-2-one melting at 182°-184°.

Aufarbeitung

  1. customThe starting material is prepared
  2. temperaturecooled in a dry ice-acetone bath
  3. stirringthe mixture stirred
  4. temperaturewith said cooling for 2 hours
  5. customIt is quenched by the slow addition of 150 ml of water
  6. extractionthe mixture is extracted with chloroform
  7. customthe extract is dried
  8. customevaporated
  9. customThe residue is crystallized from diethyl ether
  10. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9c3996ee68974fc0a4fa11f5e0daba01
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173633

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