Hydrochloric Acid → 2-Chloropyridine-3-sulfonyl chloride

HRID 1782222Notes

Reaction equation

HRID 1782222 reaction equation
N[C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+].[S:13](=[O:15])=[O:14].[ClH:16]>>[Cl:8][C:3]1[C:2]([S:13]([Cl:16])(=[O:15])=[O:14])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 805282-Chloro-3-pyridylamineHCID 23668193Sodium Nitrite

Product 1

HCID 102199682-Chloropyridine-3-sulfonyl chlorideYield 42%

Procedure

Under ice-cooling, thionyl chloride (24 mL) was added dropwise over 1 hr to water (140 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 3-amino-2-chloropyridine (10 g) was added to concentrated hydrochloric acid (80 mL) and the mixture was stirred. An aqueous solution (25 mL) of sodium nitrite (5.75 g) was added dropwise while keeping the inside temperature at not higher than 5° C., and the mixture was further stirred for 15 min. The reaction mixture was gradually added at 5° C. to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (140 mg). Under ice-cooling, the mixture was further stirred for 30 min, and the precipitate was collected by filtration and washed with water and ethanol to give the title compound (yield 6.99 g, 42%).

Workup

  1. additioncontaining solution
  2. temperatureSeparately, under ice-cooling
  3. customhigher than 5° C.
  4. stirringthe mixture was further stirred for 15 min
  5. additioncontaining solution
  6. temperatureUnder ice-cooling
  7. stirringthe mixture was further stirred for 30 min
  8. filtrationthe precipitate was collected by filtration
  9. washwashed with water and ethanol

Sources & evidence

ORD record
ord-35d51a9a1d2749fc9c60ce097cc97ef4
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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