Acetic Acid → 5,6-dichloropyridine-3-sulfonyl Chloride

HRID 464622Notes

Reaction equation

HRID 464622 reaction equation
N[C:2]1[CH:3]=[C:4]([Cl:9])[C:5]([Cl:8])=[N:6][CH:7]=1.[N+]([O-])([O-])=O.[Na+].C(O)(=O)C.[S:19](=[O:21])=[O:20].[ClH:22]>O>[Cl:9][C:4]1[CH:3]=[C:2]([S:19]([Cl:22])(=[O:21])=[O:20])[CH:7]=[N:6][C:5]=1[Cl:8]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24268Sodium NitrateHCID 145952195-Amino-2,3-dichloropyridine

Product 1

HCID 47369115,6-dichloropyridine-3-sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

5-Amino-2,3-dichloropyridine (20.0 g, 123 mmol) was dissolved in 600 ml conc. HCl, and the solution cooled to 5° C. Sodium nitrate (8.5 g, 123 mmol) in 75 ml water was added dropwise, below the surface of the reaction, at such a rate that the temperature was maintained below 10° C. The reaction was stirred 15 minutes after the addition was complete. This mixture was then added rapidly to a solution of 600 ml acetic acid saturated with sulfur dioxide and containing also cupric chloride dihydrate (1.5 g), the solution cooled to 5° C. The reaction PG,38 was stirred at 5° C. for 20 minutes, then room temperature for 30 minutes and finally poured into 12 liters ice/water. The resulting solids were filtered off, washed with water, and air-dried. Yield: 17.27 g, 57 percent, m.p. 48°-51° C.

Workup

  1. temperatureat such a rate that the temperature was maintained below 10° C
  2. additionafter the addition
  3. temperaturethe solution cooled to 5° C
  4. customThe reaction PG,38
  5. stirringwas stirred at 5° C. for 20 minutes
  6. waitroom temperature for 30 minutes
  7. filtrationThe resulting solids were filtered off
  8. washwashed with water
  9. customair-dried

Sources & evidence

ORD record
ord-6def24626b4b407b81b818eb4808eeb1
Source dataset
uspto-grants-1985_10
Patent number
US04548888

Reaction notes

Loading…