Hydrochloric Acid → 3-Chloropyridine-2-sulfonamide

HRID 1154533Notes

Reaction equation

HRID 1154533 reaction equation
ClC1C(SCC2C=CC=CC=2)=[N:4]C=CC=1.ClCl.C([O-])(=O)C.[Na+].[Cl:23][C:24]1[C:25]([S:30](Cl)(=[O:32])=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=1.Cl>O.C(O)(=O)C>[Cl:23][C:24]1[C:25]([S:30]([NH2:4])(=[O:32])=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24526ChlorineHCID 517045Sodium Acetate2×HCID 179110873-Chloropyridine-2-sulfonyl chloride2×HCID 19881832Pyridine, 3-chloro-2-[(phenylmethyl)thio]-

Product 1

HCID 146531913-Chloropyridine-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
-30 °C

Procedure

53.0 Grams (0.225 mole) of 3-chloro-2-((phenylmethyl)thio)pyridine were added to 250 ml of acetic acid containing 16.2 grams (0.90 mole) of water. The mixture was cooled in an ice bath and passed in a stream of chlorine at 10°-15° C. for 31/2 hours. The resulting cold acetic acid solution was poured, with stirring, into a mixture of 180 grams (2.2 moles) of sodium acetate, 500 ml water and 250 grams crushed ice. (The sodium acetate converts the 3-chloro-2-pyridine sulfonyl chloride present as the hydrochloride, into free 3-chloro-2-pyridine sulfonyl chloride.) The resulting mixture was extracted with methylene chloride, washed with water, and dried over anhydrous sodium sulfate. The methylene chloride extract was evaporated to 150 ml and cooled to -30° C. in a dry ice bath.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. custom2 hours
  3. customcrushed ice
  4. extraction) The resulting mixture was extracted with methylene chloride
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. extractionThe methylene chloride extract
  8. customwas evaporated to 150 ml

Sources & evidence

ORD record
ord-f150ec48317d4586af92cc40b33e64e2
Source dataset
uspto-grants-1984_12
Patent number
US04490380

Reaction notes

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