Hydrochloric Acid → HCID 68641713, compound

HRID 1498924Notes

Reaction equation

HRID 1498924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[C:13](OC)(=[O:18])[C:14]([O:16][CH3:17])=[O:15].[H-].[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH2:9][C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11120Dimethyl oxalateHCID 24758Sodium hydrideHCID 194294681-(4-Chloro-2-methoxyphenyl)ethan-1-one

Product 1

HCID 68641713HCID 68641713, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To dimethylformamide (13 ml), 1-(4-chloro-2-methoxyphenyl)ethanone (3.13 g) and dimethyl oxalate (2.4 g) were added, and 60% sodium hydride suspension in oil (811 mg) was added thereto at 0° C. The mixture was stirred at a room temperature for one hour, and then heated to 50° C. and stirred for 19 hours. The mixture was allowed to cool to a room temperature, 3-N hydrochloric acid was added to the mixture. The resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated saline solution in order, then dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. In the process of the concentration, the precipitated crystal was separated by filtration to give the title compound (2.47 g, 54%).

Workup

  1. customat 0° C
  2. temperatureheated to 50° C.
  3. stirringstirred for 19 hours
  4. temperatureto cool to a room temperature
  5. extractionThe resulting mixture was subjected to extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated saline solution in order, then dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. concentrationIn the process of the concentration
  10. customthe precipitated crystal was separated by filtration

Sources & evidence

ORD record
ord-087c47f10cdc4986a67d3386de5daf13
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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