Hydrochloric Acid → HCID 58572634, compound

HRID 1920786Notes

Reaction equation

HRID 1920786 reaction equation
[Br:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:15]N1CCOCC1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.C[Mg]Br.O1CCCC1.Cl>C(#N)C>[Br:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[O:6])[CH3:15]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 152610122-Bromo-3-(trifluoromethyl)benzoic acidHCID 178418573HCID 178418573, compound

Product 1

HCID 58572634HCID 58572634, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture solution of 2-bromo-3-(trifluoromethyl)benzoic acid (2.50 g, 9.29 mmol), N, O-dimethylhydroxylamine hydrochloride (1.18 g, 12.1 mmol), N-methylmorpholine (2.1 mL, 18.6 mmol), and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3.78 g, 12.1 mmol) in acetonitrile (45 mL) was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was added with 1N aqueous hydrochloride solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran (90 mL), added with a solution (0.93 M) of methyl magnesium bromide in tetrahydrofuran (13.0 mL, 12.1 mmol) at −20° C., and stirred at room temperature for 18 hours. The reaction solution was poured over 1 N aqueous hydrochloride solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless oily substance (1.27 g, yield 44%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe resulting residue was added with 1N aqueous hydrochloride solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (90 mL)
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-76e89bad706546ada19d2795b4989672
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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