Water → HCID 13823497, compound

HRID 1906463Notes

Reaction equation

HRID 1906463 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[N:4][C:5]([S:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>CN(C)C=O>[CH3:21][S:22]([O:14][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[C:5]([S:9][CH2:10][CH:11]([CH3:12])[CH3:13])[N:4]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 178454956HCID 178454956, compound

Product 1

HCID 13823497HCID 13823497, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

6.0 g of 3,5-dichloro-6-isobutylthio-2-pyridinol and 3.0 g of anhydrous sodium carbonate were suspended in 25 ml of N,N-dimethylformamide, followed by stirring. 3.3 g of methanesulfonyl chloride was added dropwise to the suspension at 10° C. The obtained mixture was allowed to stand to lower the temperature to room temperature, heated to 50° C. and stirred for 2.5 hours. The reaction mixture was poured into 200 ml of chilled water and extracted with ether twice. The ether layer was washed with 5% aqueous caustic soda and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography (with n-hexane and toluene) to obtain 5.8 g of objective 3,5-dichloro-6-isobutylthio-2-pyridyl methanesulfonate as a colorless oil (yield: 73.8%).

Workup

  1. customto room temperature
  2. stirringstirred for 2.5 hours
  3. extractionextracted with ether twice
  4. washThe ether layer was washed with 5% aqueous caustic soda and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe obtained residue was purified by silica gel column chromatography (with n-hexane and toluene)

Sources & evidence

ORD record
ord-1005438071184640a533b8fdbeb6c7e0
Source dataset
uspto-grants-1987_03
Patent number
US04652574

Reaction notes

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