Sulfuric Acid → Megazol

HRID 2399000Notes

Reaction equation

HRID 2399000 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[C:10]([NH:12][NH:13][C:14]([NH2:16])=[S:15])=O.S(=O)(=O)(O)O>>[NH2:16][C:14]1[S:15][C:10]([C:3]2[N:2]([CH3:1])[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=2)=[N:12][N:13]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 214322521-(1-Methyl-5-nitro-2-imidazolecarbonyl)-3-thiosemicarbazide

Product 1

HCID 29698Megazol

Procedure

To 0.05 g. of 1-(1-methyl-5-nitro-2-imidazolecarbonyl)-3-thiosemicarbazide is added 0.5 ml. of conc. sulfuric acid and the mixture is heated on a steam bath for 30 minutes. Ice is added to the reaction mixture and the solid is filtered. The filtrate is made basic with sodium hydroxide and cooled in an ice bath. The solid is filtered, washed with water and dried affording 17 mg. (37%) of 2-(2-amino-1,3,4-thiaziazol-5-yl)-1-methyl-5-nitroimidazole.

Workup

  1. additionIce is added to the reaction mixture
  2. filtrationthe solid is filtered
  3. temperaturecooled in an ice bath
  4. filtrationThe solid is filtered
  5. washwashed with water
  6. customdried
  7. customaffording 17 mg

Sources & evidence

ORD record
ord-c07847071209491e9360d2edee0393a9
Source dataset
uspto-grants-1977_05
Patent number
US04026903

Reaction notes

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