Sulfuric Acid → 3-Phenoxypyridine monosulfate

HRID 65572Notes

Reaction equation

HRID 65572 reaction equation
[O:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:14](=[O:18])(=[O:17])([OH:16])[OH:15]>CC(O)C>[S:14]([OH:18])([OH:17])(=[O:16])=[O:15].[O:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 2005103-Phenoxypyridine

Product 1

HCID 69177363-Phenoxypyridine monosulfate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 523 g. of 3-phenoxypyridine in 750 ml. of 2-propanol is treated slowly with stirring with 303 g. of 98% sulfuric acid, while maintaining the temperature below 50° C. On cooling to room temperature, the mixture sets up solid. It is heated to 75° C., transferred to an acceptable container and allowed to cool to 50° C. and the crystalline product collected by filtration. The filtrate is allowed to stand at room temperature for 2 hours and the additional crystalline product is collected by filtration. The combined product is dried at reduced pressure to give 3-phenoxypyridine monosulfate, m.p. 103°-107° C. The salt is recrystallized from acetonitrile; after drying at reduced pressure it melts at 107°-109° C.

Workup

  1. temperatureIt is heated to 75° C.
  2. temperatureto cool to 50° C.
  3. filtrationthe crystalline product collected by filtration
  4. filtrationthe additional crystalline product is collected by filtration
  5. customThe combined product is dried at reduced pressure

Sources & evidence

ORD record
ord-ec3ac8f165b84fa19cb58a6928bed7b5
Source dataset
uspto-grants-1978_12
Patent number
US04128555

Reaction notes

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