Ammonium Hydroxide → 6-chloropyridine-3-sulfonamide

HRID 1680387Notes

Reaction equation

HRID 1680387 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][N:3]=1.[OH-].[NH4+:13]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH2:13])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 12015126-chloropyridine-3-sulfonamide

Procedure

2-Chloro-5-chlorosulfonylpyridine (2.84 g, 0.0134 mole) was added to concentrated ammonium hydroxide (50 ml) and the mixture was boiled. After adding more concentrated ammonium hydroxide (50 ml), and extending boiling until the reaction volume was approximately 50 ml, the reaction mixture was cooled in an ice bath to cause precipitation of the product. The solid was collected by filtration, washed with water and air dried; yield, 2.17 g (84 percent), m.p. 153° to 155° C. A melting point of 155° to 156° C. was observed after recrystallization from water.

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. customprecipitation of the product
  3. filtrationThe solid was collected by filtration
  4. washwashed with water and air
  5. customdried
  6. customyield
  7. customafter recrystallization from water

Sources & evidence

ORD record
ord-179ed32baf2441ed90ee662585ee6ba8
Source dataset
uspto-grants-1981_06
Patent number
US04273706

Reaction notes

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