Methanesulfonyl chloride → HCID 22734208, compound

HRID 2084767Notes

Reaction equation

HRID 2084767 reaction equation
O[CH2:2][C:3]1[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[C:6]([O:14][CH3:15])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.CS(Cl)(=O)=O.[SH:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C(Cl)Cl.O>[CH3:15][O:14][C:6]1[C:7]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8]=2[C:3]([CH2:2][S:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22734077HCID 22734077, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 22734208HCID 22734208, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 48a (2.0 g) obtained in Step A was dissolved in methylene chloride (100 ml), and then diisopropylethylamine (5.0 ml) and methanesulfonyl chloride (0.8 ml) were added thereto, followed by stirring at room temperature for one hour. At the same temperature, 4-mercaptopyridine (1.4 g) was added to the reaction solution, and the mixture was stirred for 30 minutes. Water was added to the reaction solution and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to give Compound 48 (1.4 g, 48.3%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-d7c87aa8e8d946a98199182ac4ee37dd
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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