Acetic Acid → Temozolomide

HRID 1433127

Reaktionsgleichung

Reaktionsgleichung von HRID 1433127
[CH3:1][N:2]1[N:11]=[N:10][C:9]2[N:5]([CH:6]=[N:7][C:8]=2[C:12]([NH2:14])=[O:13])[C:3]1=[O:4].Cl.C(#N)C.C(O)(=O)C>O>[CH3:1][N:2]1[N:11]=[N:10][C:9]2[N:5]([CH:6]=[N:7][C:8]=2[C:12]([NH2:14])=[O:13])[C:3]1=[O:4]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 11658676HCID 11658676, Verbindung

Produkt 1

HCID 5394TemozolomideAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
61.5 °C

Versuchsvorschrift

A 500 ml reaction vessel equipped with a magnetic stirrer and a reflux condenser was charged with Temozolomide hydrochloride (11.7 grams, 0.0507 mol), acetonitrile (79 ml), acetic acid (2.5 ml) and water (96.5 ml). The reaction mixture was heated to 60-63° C. and stirring was maintained at this temperature for about 10 minutes. The reaction mixture was filtered at this temperature and then cooled to 5° C. for about half an hour to enable crystallization. The crystals thus obtained were collected and washed with water (2×20 ml) and cold acetone (20 ml). The crystals were dried at 40° C. in vacuum to obtain 8.54 grams (0.044 mol) of free Temozolomide base (86.7% yield). Purity (by HPLC): 99.96%.

Aufarbeitung

  1. customA 500 ml reaction vessel
  2. customequipped with a magnetic stirrer and a reflux condenser
  3. temperaturewas maintained at this temperature for about 10 minutes
  4. filtrationThe reaction mixture was filtered at this temperature
  5. temperaturecooled to 5° C. for about half an hour
  6. customcrystallization
  7. customThe crystals thus obtained
  8. customwere collected
  9. washwashed with water (2×20 ml) and cold acetone (20 ml)
  10. customThe crystals were dried at 40° C. in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c0186e0b00f44217a3cc39fbeb4d5f8f
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612202B2

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