Hydrochloric Acid → 2-Chloro-5-pyridinesulfonyl chloride

HRID 2090620Notes

Reaction equation

HRID 2090620 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.N([O-])=O.[Na+].[S:13](=[O:15])=[O:14].[ClH:16]>>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([S:13]([Cl:16])(=[O:15])=[O:14])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 793055-Amino-2-chloropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideYield 58%

Procedure

Under ice-cooling, thionyl chloride (12 mL) was added dropwise over 1 hr to water (70 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 5-amino-2-chloropyridine (5.0 g) was added to concentrated hydrochloric acid (40 mL) and the mixture was stirred. An aqueous solution (12.5 mL) of sodium nitrite (2.88 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 (70 mg). Under ice-cooling, the mixture was further stirred for 30 min. The precipitate was collected by filtration, and washed with water and ethanol to give the title compound (yield 4.79 g, 58%).

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-c4ff9c85cb894f888b85147987d6a49d
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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