Hydrochloric Acid → HCID 13432077, compound

HRID 916559Notes

Reaction equation

HRID 916559 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[Cl:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]#[N:21])[CH:15]=[CH:16][C:17]=1[Cl:18].Cl>C1(C)C=CC=CC=1.O>[C:20]([CH:19]([C:14]1[CH:15]=[CH:16][C:17]([Cl:18])=[C:12]([Cl:11])[CH:13]=1)[C:1]([O:5][CH2:6][CH3:7])=[O:8])#[N:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 13432077HCID 13432077, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl carbonate (4.1 mL, 33.88 mmol) in toluene (150 mL) at r.t, sodium hydride (1.43 g, 60% in mineral oil, 35.75 mmol) and 3,4-dichlorophenyl acetonitrile (6.34 g, 34.09 mmol) were added. The content was stirred at 80° C. overnight. After cooling to r.t, HCl was added (1 N in H2O, 100 mL). The content was extracted with ethyl acetate (3×). The combined organic layer was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography with hexane/ethyl acetate (6/1) to give 7.42 g product (85% yield) as brown oil. 1H NMR (400 MHz, CDCl3) δ[ppm]: 7.60 (1H, broad s), 7.54 (1H, d, J=8.3 Hz), 7.35 (1H, broad d, J=8.3 Hz), 4.72 (1H, s), 4.29 (2H, q, J=14.2 Hz, 7.0 Hz), 1.28 (3H, t, J=6.7 Hz). LRMS calculated for C11H9Cl2NO2 M+ 257. found 257.

Workup

  1. temperatureAfter cooling
  2. extractionThe content was extracted with ethyl acetate (3×)
  3. washThe combined organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography with hexane/ethyl acetate (6/1)

Sources & evidence

ORD record
ord-5a248d354f274073848b6b3ec0f83770
Source dataset
uspto-grants-2007_09
Patent number
US07271172B2

Reaction notes

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