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

HRID 472082Notes

Reaction equation

HRID 472082 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 (15 g, 86.7 mmol) portionwise. The reaction mixture was then heated at reflux for 3 hrs. 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, washing with cold water and petroleum ether to provide the title compound as an orange-yellow solid (18.1 g, 77% yield). MS (ES)+ m/e 272.8 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-dbfb565570964ccf959396daedf9eaf0
Source dataset
uspto-grants-2014_01
Patent number
US08633187B2

Reaction notes

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