Sodium Acetate → HCID 22164277, compound

HRID 1087947Notes

Reaction equation

HRID 1087947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:13][C:14]2([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[N:18]=3)[O:16][CH2:15]2)[CH3:12])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:24].[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>C(O)(=O)C>[C:25]([O:28][CH2:15][C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[N:18]=1)([OH:16])[CH2:13][N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:24])[CH:4]=1)(=[O:9])=[O:10])[CH3:12])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 15008802HCID 15008802, compound

Product 1

HCID 22164277HCID 22164277, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7.0 g of 1-[N-(4-chloro-3-methylbenzenesulfonyl)-N-methylamino]-2-(6-chloropyridin-2-yl)-2,3-epoxypropane, 3.70 g of anhydrous sodium acetate and 60 ml of acetic acid was stirred at 100° C. for 12 hours. The reaction mixture was concentrated under a reduced pressure and 100 ml of water was added thereto. The mixture was extracted with ethyl acetate, subsequently washed with water, saturated aqueous solution of sodium bicarbonate and saturated saline solution in that order, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluted with ethyl acetate - n-hexane 1:3 ) to obtain 5.87 g of the objective compound.

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure and 100 ml of water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washsubsequently washed with water, saturated aqueous solution of sodium bicarbonate and saturated saline solution in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate - n-hexane 1:3 )

Sources & evidence

ORD record
ord-32b6276c85f14836890fba27c5cf5748
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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