Carbon Tetrachloride → HCID 178489887, compound

HRID 599638Notes

Reaction equation

HRID 599638 reaction equation
C(Cl)(Cl)(Cl)[Cl:2].[C:6]([CH2:8][NH:9][C:10](=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]2)=[C:15]([O:25][CH3:26])[CH:14]=1)#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Cl:2][C:6]1[N:7]=[C:10](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[C:15]([O:25][CH3:26])[CH:14]=2)[NH:9][CH:8]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 86615147HCID 86615147, compound

Product 1

HCID 178489887HCID 178489887, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

Carbon tetrachloride (0.326 mL) was added to a solution of (E)-N-cyanomethyl-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide (400 mg) and triphenylphosphine (888 mg) in acetonitrile (20 mL), and the reaction solution was stirred at 45° C. for 12 hours. The reaction solution was concentrated under reduced pressure. Ethyl acetate and saturated sodium bicarbonate water were added to the resulting residue, and the organic layer was separated. The resulting organic layer was sequentially washed with water and brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate) to obtain 76 mg of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionEthyl acetate and saturated sodium bicarbonate water were added to the resulting residue
  3. customthe organic layer was separated
  4. washThe resulting organic layer was sequentially washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-0d7566125d624712b4cc19f3900851b0
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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