Sulfuric Acid → 2-bromo-5-methyl-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one

HRID 908636Notes

Reaction equation

HRID 908636 reaction equation
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[S:11][C:10]([N-:12][CH2:13][CH2:14][C:15](=O)[CH3:16])=[N:9][N:8]=1>C(=O)([O-])[O-].[Na+].[Na+]>[Br:6][C:7]1[S:11][C:10]2=[N:12][C:13](=[O:2])[CH:14]=[C:15]([CH3:16])[N:9]2[N:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86619483N-(5-bromo-[1,3,4]thiadiazol-2-yl)-3-oxo-butylamide

Product 1

HCID 6373782-bromo-5-methyl-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To concentrated sulfuric acid (10 ml) heated to 60° C. was added the compound (1.3 g) obtained in Step 2 in divided portions, and the mixture was stirred at the same temperature for 3 hr. The reaction mixture was poured into ice (100 g), and the mixture was neutralized with an aqueous solution (100 ml) of sodium carbonate (20 g). The organic layer was extracted with chloroform (50 ml), and dried to give the title compound (810 mg).

Workup

  1. extractionThe organic layer was extracted with chloroform (50 ml)
  2. customdried

Sources & evidence

ORD record
ord-0d1b30102b404cd0adee87b1ef149e39
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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