Hydrochloric Acid → HCID 23364527, compound

HRID 2073838Notes

Reaction equation

HRID 2073838 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].[F:21][C:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[C:26]([F:32])[C:25]([F:33])=[CH:24][C:23]=1[C:34]1[O:35][CH2:36][C:37]([CH3:40])([CH3:39])[N:38]=1.CI.Cl>C1COCC1>[F:21][C:22]1[C:27]([C:28]([F:31])([F:29])[F:30])=[C:26]([F:32])[C:25]([F:33])=[C:24]([CH3:1])[C:23]=1[C:34]1[O:35][CH2:36][C:37]([CH3:40])([CH3:39])[N:38]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 23364532HCID 23364532, compoundHCID 178418339Butyllithium

Product 1

HCID 23364527HCID 23364527, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.12 g (11.0 mmol) of diisopropylamine in 5 ml of THF was cooled to 0° C. under nitrogen, treated with 4.0 ml of 2.5M n-butyllithium, and stirred for 10 minutes. This lithium diisopropylamide solution was added dropwise to a solution of 2.36 g (8 mmol) of 2-[2,4,5-trifluoro-3-(trifluoromethyl)-phenyl]-4,4-dimethyl-2-oxazoline in 5 ml of THF at -78° C. The solution was stirred at -78° C. for one hour, then quenched with 2.24 g (16 mmol) of methyl iodide. The mixture was allowed to warm slowly to room temperature, stirred for one hour, and poured into 10 ml of 1N HCl. This solution was extracted with ether, and the extract was washed with water, dried over magnesium sulfate, and concentrated to give 2.28 g of the title compound.

Workup

  1. stirringThe solution was stirred at -78° C. for one hour
  2. stirringstirred for one hour
  3. extractionThis solution was extracted with ether
  4. washthe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6795478790ef4bdb8ed11a7caad0a634
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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