Methanesulfonyl chloride → HCID 86603196, compound

HRID 2055822Notes

Reaction equation

HRID 2055822 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[O:6][CH:7]([OH:9])[CH3:8])[CH3:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[O:6][CH:7]([OH:9])[CH3:8])[CH3:2].[CH3:14][S:15]([O-:17])(=[O:3])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69224500HCID 69224500, compound

Product 1

HCID 86603196HCID 86603196, compoundYield 159.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-2.5 °C

Procedure

50.0 g (0.28 mol) o-ethoxyphenoxyethanol and 197 g pyridine are added into a reaction flask, stirred until they are fully dissolved, and then cooled to −5 to 0° C. During stirring, 53.1 g (0.46 mol) methyl sulfonyl chloride is added gradually into the flask at a temperature controlled at −5 to 0° C. After addition, the reaction lasts for 3 to 4 hours at a temperature of 0 to 5° C. After the reaction is complete, the reacting solution is added gradually into 350 ml ice water under stirring at a temperature controlled at 0 to 5° C. to isolate gradually white solids, which are then filtered, and the filter cake is rinsed three times with 150 ml water until there is no smell of pyridine, and then dried to obtain 61.9 g title compound. Yield: 85.0%; purity: 99.83% (HPLC).

Workup

  1. dissolutionare fully dissolved
  2. stirringDuring stirring
  3. customcontrolled at −5 to 0° C
  4. additionAfter addition
  5. stirringunder stirring at a temperature
  6. customcontrolled at 0 to 5° C.
  7. customto isolate gradually white solids, which
  8. filtrationare then filtered
  9. washthe filter cake is rinsed three times with 150 ml water until there
  10. customdried

Sources & evidence

ORD record
ord-2fa0db1706c74765867d377c2ab6b7d3
Source dataset
uspto-grants-2008_02
Patent number
US07332621B2

Reaction notes

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