Hydrochloric Acid → HCID 19702329, compound

HRID 1927300Notes

Reaction equation

HRID 1927300 reaction equation
[Br:1][C:2]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH3:16][Mg]Br.C(OCC)(=O)C.Cl>O1CCCC1>[Br:1][C:2]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4](=[O:5])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 58572498HCID 58572498, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19702329HCID 19702329, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 2-bromo-N,3-dimethoxy-N-methylbenzamide (16.8 g, 61.5 mmol) which had been obtained in Reference example 1(1a) was dissolved in tetrahydrofuran (300 mL), and added dropwise with a 1.0 M solution of methyl magnesium bromide in tetrahydrofuran (123 mL, 123 mmol) at 0° C. Upon the completion of the dropwise addition, the temperature of the reaction solution was raised to room temperature and stirred for 15 hours. The reaction solution was added with ethyl acetate and 1 N aqueous hydrochloric acid solution for fractionation, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0 to 60:40, V/V) to give the title compound as a colorless oily substance (12.7 g, yield 90%).

Workup

  1. additionUpon the completion of the dropwise addition
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0 to 60:40, V/V)

Sources & evidence

ORD record
ord-97bff07f667049dfa9cd4b07a1edaa5f
Source dataset
uspto-grants-2012_05
Patent number
US08183272B2

Reaction notes

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