Phosphorus oxychloride → HCID 67067434, compound

HRID 599593Notes

Reaction equation

HRID 599593 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:15]=[CH:16]/[C:17]([NH:19][NH:20][C:21](=[O:33])[CH:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:23][CH2:24]O)=O)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.P(Cl)(Cl)([Cl:36])=O>>[Cl:36][CH2:24][CH2:23][CH:22]([C:21]1[O:33][C:17](/[CH:16]=[CH:15]/[C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:19][N:20]=1)[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67067277HCID 67067277, compound

Product 1

HCID 67067434HCID 67067434, compound

Procedure

A solution of 2-(4-fluorophenyl)-4-hydroxybutyric acid N′-{(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide (224 mg) in phosphorus oxychloride (1 mL) was stirred at 120° C. for two hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. Ethyl acetate and saturated sodium bicarbonate water were added to the residue, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent solvent: ethyl acetate→ethyl acetate:methanol=3:1) to obtain 87 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. concentrationconcentrated under reduced pressure
  3. additionEthyl acetate and saturated sodium bicarbonate water were added to the residue
  4. customthe organic layer was separated
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent solvent: ethyl acetate→ethyl acetate:methanol=3:1)

Sources & evidence

ORD record
ord-0780113909ee4874ba1de18a8141f666
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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