Dichloromethane → HCID 18997188, compound

HRID 374492Notes

Reaction equation

HRID 374492 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].ClCCl.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]([CH2:21][OH:22])[CH2:19][O:18][C:17]2=[O:23])=[CH:12][CH:11]=1>C(N(CC)CC)C>[CH3:1][S:2]([O:22][CH2:21][CH:20]1[CH2:19][O:18][C:17](=[O:23])[N:16]1[C:13]1[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 53874791HCID 53874791, compound

Product 1

HCID 18997188HCID 18997188, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methanesulfonyl chloride (3.0 g) was added dropwise to a dichloromethane (50 ml) solution of 5.30 g of 3-(4-chlorophenyl)-2-oxooxazolidin-4-ylmethyl alcohol obtained in Reference Example 17 and 8.5 ml of triethylamine with ice-cooling, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was washed with water, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by chloroform-ethanol gradient elution to give 6.50 g of the title compound (yield 91%).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by chloroform-ethanol gradient elution

Sources & evidence

ORD record
ord-4aa025bb1bdd463a9694b386fcebb213
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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