Dimethyl Sulfide → 1-Benzyl-1,4,7,10-tetraazacyclododecane

HRID 1488360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488360
[CH2:1]([N:8]1[CH2:19][C:18](=O)[NH:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][NH:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC>O1CCCC1>[CH2:1]([N:8]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 157028294-Benzyl-1,4,7,10-tetraazacyclododecane-2,6-dione

Produkt 1

HCID 100840821-Benzyl-1,4,7,10-tetraazacyclododecane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 890 mg (3.07 mmol) of 1-benzyl-3,11-dioxo-1,4,7,10-tetraazacyclododecane in tetrahydrofuran under nitrogen was added 2.64 ml of 8M borane-methyl sulfide complex (21.1 mol, 7 equivalents). The mixture was heated to reflux allowing the methyl sulfide to distill out of the reaction flask. After 2 hours, the reaction was quenched by the addition of 12 ml 1.8M hydrochloric acid in methanol and refluxed for an additional 3 hours. Volatiles were removed by evaporation, and the solid resuspended in methanol and reevaporated.

Aufarbeitung

  1. additionwas added 2.64 ml of 8M borane-methyl sulfide complex (21.1 mol, 7 equivalents)
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. distillationto distill out of the reaction flask
  5. customthe reaction was quenched by the addition of 12 ml 1.8M hydrochloric acid in methanol
  6. temperaturerefluxed for an additional 3 hours
  7. customVolatiles were removed by evaporation
  8. customreevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a615d76bb934411d9115296ff4afe4a6
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674470

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