Sodium Chloride → 2-Bromo-imidazo[2,1-b][1,3,4]thiadiazole-5-sulfonic acid

HRID 1043667Notes

Reaction equation

HRID 1043667 reaction equation
[Br:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.[Cl-].[Na+].[OH:12][S:13](O)(=[O:15])=[O:14].O=S(=O)=O>>[Br:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([S:13]([OH:15])(=[O:14])=[O:12])[N:4]2[N:3]=1

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 24681Fuming sulfuric acidHCID 436679232-Bromoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 866562332-Bromo-imidazo[2,1-b][1,3,4]thiadiazole-5-sulfonic acid

Conditions

Temperature
80 °C

Procedure

The starting 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (2.0 g; 9.9 mmol) was dissolved in oleum (4.0 mL) and the resulting solution was heated at 80° C. for 8 hours. The reaction was allowed to cool to room temperature and then poured onto crushed ice. One spoon of sodium chloride was added and the resulting precipitate was isolated by vacuum filtration and washed with cold water. It was dried by azeotrope distillation with toluene. The title compound 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole-5-sulfonic acid was isolated as a beige solid, (2.33 g; 83% yield).

Workup

  1. temperatureto cool to room temperature
  2. additionpoured
  3. customonto crushed ice
  4. customthe resulting precipitate was isolated by vacuum filtration
  5. washwashed with cold water
  6. dry with materialIt was dried by azeotrope distillation with toluene

Sources & evidence

ORD record
ord-4ef510fc8e2d41f6a0f5e0b27022c7aa
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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