Sulfuric Acid → Temozolomide

HRID 8288

Reaction equation

HRID 8288 reaction equation
CC([NH:5][C:6]([C:8]1[N:9]=[CH:10][N:11]2[CH2:16][N:15]([CH3:17])[N:14]=[N:13][C:12]=12)=[O:7])(C)C.[OH:18]S(O)(=O)=O>>[CH3:17][N:15]1[C:16](=[O:18])[N:11]2[CH:10]=[N:9][C:8]([C:6]([NH2:5])=[O:7])=[C:12]2[N:13]=[N:14]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 22015426HCID 22015426, compound

Product 1

HCID 5394Temozolomide

Procedure

t-Butyl-Temozolomide 8 (4.01 g, 16.023 mmol) and conc. H2SO4 (8 mL) (Fisher Scientific) were placed into a 50 mL flask equipped with a stirrer bar. The mixture was stirred for 2 hours at room temperature and then slowly poured into ice-cold EtOH (160 mL). A white precipitate formed, which was collected by vacuum filtration and washed with ice-cold EtOH (10 mL). The solid was dried under vacuum (20 mm Hg, room temperature, 72 hours) to yield 2.63 g of 9 (13.546 mmol, 98.4% pure against a standard sample by HPLC analysis)

Workup

  1. customequipped with a stirrer bar
  2. customA white precipitate formed
  3. filtrationwhich was collected by vacuum filtration
  4. washwashed with ice-cold EtOH (10 mL)
  5. customThe solid was dried under vacuum (20 mm Hg, room temperature, 72 hours)

Sources & evidence

ORD record
ord-0462536148484ddba9052e5d961cae80
Source dataset
uspto-grants-2006_08
Patent number
US07087751B2

Linked notes

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