Hydrochloric Acid → 1-Chloro-3-isopropylsulphonylpyridine

HRID 1591280Notes

Reaction equation

HRID 1591280 reaction equation
C([C:3]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:4][CH:5]=[CH:6][N:7](C)[CH3:8])#N.[ClH:16].O.[OH-].[Na+]>C(O)(C)C>[Cl:16][N:7]1[CH:6]=[CH:5][CH:4]=[C:3]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 545474291-Cyano-1-isopropylsulphonyl-4-dimethylamino-1,3-butadiene2×

Product 1

HCID 197667541-Chloro-3-isopropylsulphonylpyridineYield 51.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The 1-cyano-1-isopropylsulphonyl-4-dimethylamino-1,3-butadiene (34 g, 0.15 mol) obtained in (a) above was dissolved in isopropanol (350 ml). The solution was then heated to reflux and saturated with dry hydrogen chloride. After about 20 hours, the solution was cooled and poured into water and crushed ice. This solution was then neutralised with sodium hydroxide solution and extracted with toluene (5×100 ml). The combined extracts were then evaporated and the remaining brown syrup purified over silica using 1:1 toluene:ethyl acetate as eluant to leave an oil which yielded 7 g 1-chloro-3-isopropylsulphonylpyridine as yellow crystals, m.pt. 82°-84° C., after stirring with petroleum ether. Yield: 51.5% of the theoretical.

Workup

  1. temperatureThe solution was then heated
  2. temperaturethe solution was cooled
  3. customcrushed ice
  4. extractionextracted with toluene (5×100 ml)
  5. customThe combined extracts were then evaporated
  6. customthe remaining brown syrup purified over silica using 1:1 toluene
  7. customethyl acetate as eluant to leave an oil which

Sources & evidence

ORD record
ord-ff780cc640a043e192c70029634c1275
Source dataset
uspto-grants-1993_04
Patent number
US05206372

Reaction notes

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