Hydrochloric Acid → HCID 178463848, compound

HRID 2361556Notes

Reaction equation

HRID 2361556 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:19]=[CH:18][C:12]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:11][CH:10]=1.[P:20]([O-:27])(OCC)OCC.Cl>O1CCCC1.C(OCC)(=O)C.O>[CH2:14]([N:13]([CH2:5][CH3:6])[C:12]1[CH:18]=[CH:19][C:9]([PH:20](=[O:27])[C:9]2[CH:19]=[CH:18][C:12]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:11][CH:10]=2)=[CH:10][CH:11]=1)[CH3:15]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 78391,2-DibromoethaneHCID 16328Benzenamine, 4-bromo-N,N-diethyl-HCID 3780918DiethylphosphiteHCID 5462224Magnesium

Product 1

HCID 178463848HCID 178463848, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen stream, a solution of magnesium (5.3 g, 1.00 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in tetrahydrofuran (30 mL) was stirred at room temperature for 30 min. A solution of 4-bromo-N,N-diethylaniline (49.7 g, 0.217 moL) in tetrahydrofuran (100 mL) was added to the mixture at 25° C. to 35° C. over 1 hr, and the mixture was stirred at 40° C. for 40 min. Then, a solution of diethyl phosphite (9.20 g, 0.30 equivalent) in tetrahydrofuran (20 mL) was added to the mixture at 20° C. to 25° C. for 15 min. 6M Hydrochloric acid (30 mL) and water (30 mL) were added to the mixture at 3° C. to 15° C., and then ethyl acetate (100 mL) was added thereto. The mixture was partitioned, and the organic layer was washed successively with water (30 mL), 5%-aqueous sodium hydrogen carbonate solution (30 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate and filtered naturally. Then, the organic layer was concentrated under reduced pressure. The residue was recrystallized from n-heptane to give the title compound (19.82 g, white crystals). yield 87%. melting point 129.1° C.

Workup

  1. customThe mixture was partitioned
  2. washthe organic layer was washed successively with water (30 mL), 5%-aqueous sodium hydrogen carbonate solution (30 mL) and saturated brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered naturally
  5. concentrationThen, the organic layer was concentrated under reduced pressure
  6. customThe residue was recrystallized from n-heptane

Sources & evidence

ORD record
ord-f4a0d9479b7e4262bb73f629ee9024e8
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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