Chlorosulfonic acid → 2-Amino-5-bromopyridine-3-sulfonyl chloride

HRID 2036798Notes

Reaction equation

HRID 2036798 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1>>[NH2:13][C:10]1[C:9]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:8][C:7]([Br:6])=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 706222-Amino-5-bromopyridine

Product 1

HCID 533020262-Amino-5-bromopyridine-3-sulfonyl chlorideYield 77%

Procedure

To a cooled (0° C.) solution of chlorosulfonic acid (58 mL) under vigorous stirring was added 5-bromo-2-pyridinamine (86.7 mmol) portion wise. The reaction mixture was then heated at reflux for 3 h. Upon cooling to room temperature, the reaction mixture was poured over ice (100 g) with vigorous stirring. The resulting yellow precipitate was collected by suction filtration, washed with cold water and petroleum ether to provide 2-amino-5-bromopyridine-3-sulfonyl chloride (18 g, 77% yield) as an orange-yellow solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 3 h
  3. filtrationThe resulting yellow precipitate was collected by suction filtration
  4. washwashed with cold water and petroleum ether

Sources & evidence

ORD record
ord-2d801ec605e64b9ebc70e1df503b5984
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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