Acetic Acid → Temozolomide

HRID 1433128Notes

Reaction equation

HRID 1433128 reaction equation
[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.CC(C)=O.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]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 180AcetoneHCID 11658676Temozolomide hydrochloride

Product 1

HCID 5394TemozolomideYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A 500 ml reaction vessel equipped with a magnetic stirrer and a reflux condenser was charged with Temozolomide hydrochloride (7.2 gram, 0.031 mol), acetone (85 ml), acetic acid (1.8 ml) and water (90 ml). The reaction mixture was heated to reflux and stirring was maintained at this temperature for about 10 minutes. The reaction mixture was filtered at elevated 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 5.3 grams (0.027 mol) of free Temozolomide base (88% yield).

Workup

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

Sources & evidence

ORD record
ord-a7912e26033a4dc29f3d6e1fb51d3084
Source dataset
uspto-grants-2009_11
Patent number
US07612202B2

Reaction notes

Loading…