Hydrochloric Acid → HCID 60209327, compound

HRID 1801743Notes

Reaction equation

HRID 1801743 reaction equation
CON(C)[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:6]=1.[CH3:23][Mg]Br.Cl>C1COCC1.CC(OC)(C)C>[F:20][C:17]([F:18])([F:19])[CH2:16][O:15][C:7]1[CH:6]=[C:5]([C:4](=[O:21])[CH3:23])[CH:10]=[CH:9][C:8]=1[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86602234N-Methoxy-N-methyl-3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 60209327HCID 60209327, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-methoxy-N-methyl-3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzamide from step 7 (10.467 g, 32 mmol) in THF (100 mL) at −5° C. was added methylmagnesium bromide (3 M in Et2O, 21.1 mL, 64 mmol). The mixture was stirred at 0° C. for 15 min, then warmed up to 23° C., stirring was continued for further 1.5 h at 23° C. Cooled to 0° C., 1 N HCl (150 mL) was added dropwise, stirring was continued at 23° C. for 15 min, the mixture was diluted with TBME, the phases were separated, the organic layer was washed with water and brine, dried over MgSO4. Removal of the solvent in vacuum left a yellow solid (9.021 g, 100%), which was used without further purification. MS (EI) 286.1 [M].

Workup

  1. temperaturewarmed up to 23° C.
  2. stirringstirring
  3. waitwas continued for further 1.5 h at 23° C
  4. temperatureCooled to 0° C.
  5. stirringstirring
  6. waitwas continued at 23° C. for 15 min
  7. customthe phases were separated
  8. washthe organic layer was washed with water and brine
  9. dry with materialdried over MgSO4
  10. customRemoval of the solvent in vacuum
  11. waitleft a yellow solid (9.021 g, 100%), which
  12. customwas used without further purification

Sources & evidence

ORD record
ord-0f7a3f38be1543d5957d3dd6262e169f
Source dataset
uspto-grants-2013_01
Patent number
US08349844B2

Reaction notes

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