Sulfuric Acid → 3-Amino-5-methylmercapto-thiazolo-(4,5-c)-isothiazole

HRID 262027Notes

Reaction equation

HRID 262027 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:9](=[S:11])[NH2:10])=[C:6]([NH2:8])[N:7]=1.S(=O)(=O)(O)O.BrBr>>[NH2:10][C:9]1[S:11][N:8]=[C:6]2[N:7]=[C:3]([S:2][CH3:1])[S:4][C:5]=12

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 12526353HCID 12526353, compound

Product 1

HCID 125263693-Amino-5-methylmercapto-thiazolo-(4,5-c)-isothiazoleYield 84%

Conditions

Temperature
45 °C

Procedure

15 parts of 2-methylmercapto-4-amino-5-thiocarbamoylthiazole are introduced, at 30° C., into 100 parts of sulfuric acid (of 98 percent strength by weight), containing 0.5 part of bromine. When the evolution of gas has subsided (after 10 minutes), the mixture is stirred for 10 minutes at 45° C. and is then poured on to 300 parts of ice, the batch is filtered and the filter residue is stirred with 100 parts of aqueous 30 percent by weight ammonia solution and filtered off. 12.5 parts of 3-amino-5-methylmercapto-thiazolo-(4,5-c)-isothiazole (84% of theory) of melting point 160°-166° C. are obtained.

Workup

  1. custom(after 10 minutes)
  2. additionis then poured on to 300 parts of ice
  3. filtrationthe batch is filtered
  4. stirringthe filter residue is stirred with 100 parts of aqueous 30 percent by weight ammonia solution
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-f9c1365b39d5403fbc2afba3be3cc34e
Source dataset
uspto-grants-1979_05
Patent number
US04153607

Reaction notes

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