Hydrochloric Acid → 6-Bromopyridine-3-sulfonyl chloride

HRID 1696870Notes

Reaction equation

HRID 1696870 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([Br:8])=[N:6][CH:7]=1.N([O-])=O.[Na+].[S:13](=[O:15])=[O:14].[ClH:16]>O.C(O)(=O)C.O.O.[Cu](Cl)Cl>[Br:8][C:5]1[N:6]=[CH:7][C:2]([S:13]([Cl:16])(=[O:15])=[O:14])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 6428116-Bromopyridin-3-amineHCID 23668193Sodium Nitrite

Product 1

HCID 529882526-Bromopyridine-3-sulfonyl chloride

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a cooled (0° C.-5° C.) stirred solution of 5-amino-2-bromopyridine (1.5 g, 8.6 mmol) in 12 N hydrochloric acid (26.5 mL), was slowly added a solution of sodium nitrite (0.66 g, 7.76 mmol) in water (7 mL). In a separate flask, sulfur dioxide was bubbled through a stirred solution of copper(II) chloride dihydrate (0.63 g, 3.50 mmol) in glacial acetic acid at 0° C. for 30 minutes, and then the diazotized reaction mixture prepared above was added. The resulting mixture was slowly warmed to room temperature and stirred for 30 minutes, then was poured into ice water (100 mL), and extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude 6-bromo-pyridine-3-sulfonyl chloride, which was immediately used in the next step.

Workup

  1. temperatureTo a cooled (0° C.-5° C.)
  2. customthe diazotized reaction mixture prepared
  3. additionabove was added
  4. extractionextracted with ethyl acetate (50 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-730c73c60a1f40b1936fce18421b3db6
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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