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

HRID 1856605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856605
[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 15702829HCID 15702829, Verbindung

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. The product was crystallized from methanol/ethyl acetate; yield 455 mg, 37%. Mass spectrum (CI): m/e 263 (M+H).

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
  9. customThe product was crystallized from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-040985857c8b4a51b7cbc63908668c26
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143274

Notizen zur Reaktion

Wird geladen…