Hydrochloric Acid → HCID 22393511, compound

HRID 1071515Notes

Reaction equation

HRID 1071515 reaction equation
C([Li])(CC)C.[CH2:6]([N:8]([CH2:18][CH3:19])[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[CH3:7].CN([CH:23]=[O:24])C.Cl>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH2:18]([N:8]([CH2:6][CH3:7])[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[CH:23]=[O:24])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 75946N,N-Diethyl-p-toluamideHCID 178418400CID 53628100

Product 1

HCID 22393511HCID 22393511, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
78 °C

Procedure

Tetramethylethyleneamine (6.20 g, 5336 mmol, 8.05 mL) was dissolved in anhydrous THF (100 mL) under argon and cooled to minus 78° C. s-Butyl lithium (1.30M, 53.36 mmol, 41.04 mL) was added to the solution slowly via syringe. The solution was stirred for 10 min at minus 78° C., then N,N-diethyl-4-methyl-benzamide (9.28 g, 48.51 mmol), dissolved in 50 mL of anhydrous THF was added to the reaction mixture over 15 min. The reaction was stirred for 1 h at minus 78° C. , the DMF (7.09 g, 97.02 mol, 7.51 mL) was added to the solution rapidly. The reaction mixture was allowed to slowly warm to room temp and stir for 12 h. The reaction mixture was poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane/ethyl acetate) Yield 7.98 g. 1H NMR (CDCl3, 300 MHz): δ 1.08 (t, 3H), 1.32 (t, 3H), 2.46 (s, 3H), 3.13 (q, 2H), 3.42 (a, 2H), 7.28 (d, J=8, 1H), 7.45 (d, J=7, 1H), 7.77 (s, 1H), 10.01 (s, 1H).

Workup

  1. additionwas added to the solution slowly via syringe
  2. additionwas added to the reaction mixture over 15 min
  3. stirringThe reaction was stirred for 1 h at minus 78° C.
  4. temperatureto slowly warm to room temp
  5. stirringstir for 12 h
  6. extractionthe aqueous layer was extracted three times with ethyl acetate
  7. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe solution was filtered
  10. customthe solvent removed under reduced pressure
  11. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-470f008f074c4236b03aca69c33f97fb
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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