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

HRID 1096787Notes

Reaction equation

HRID 1096787 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 (p100 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. additionthe reaction mixture was poured over ice (p100 g) with vigorous stirring
  4. filtrationThe resulting yellow precipitate was collected by suction filtration
  5. washwashing with cold water and petroleum ether

Sources & evidence

ORD record
ord-c9c6c9734c92483e8deb9039a9aeaf30
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Reaction notes

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