Hydrochloric Acid → N-(5-bromopyridin-3-yl)benzenesulfonamide

HRID 1695753Notes

Reaction equation

HRID 1695753 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chloride2×HCID 8176813-Amino-5-bromopyridine

Product 1

HCID 57843412N-(5-bromopyridin-3-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-3-pyridinamine (5 g) was dissolved in pyridine (150 ml) and the reaction was cooled to 0° C. in an ice-bath and stirred for 5 min. Benzenesulfonyl chloride (1.86 ml) was added dropwise and the reaction was stirred at 0° C. for 3 hr. Further benzenesulfonyl chloride (1.86 ml) was added and the reaction continued stirring for 1 hr. The reaction was neutralised with 2 M HCl and extracted with DCM (60 ml) then evaporated to dryness. The residue was dissolved in DCM and preadsorbed on fluorosil then purified by column chromatography on silica, eluting with 1-5% MeOH/DCM, to give the title compound (8 g).

Workup

  1. stirringthe reaction was stirred at 0° C. for 3 hr
  2. stirringthe reaction continued stirring for 1 hr
  3. extractionextracted with DCM (60 ml)
  4. customthen evaporated to dryness
  5. dissolutionThe residue was dissolved in DCM
  6. customthen purified by column chromatography on silica
  7. washeluting with 1-5% MeOH/DCM

Sources & evidence

ORD record
ord-70354769617245258533d00922bef3e1
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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