Acetic Acid → HCID 86753043, compound

HRID 482446Notes

Reaction equation

HRID 482446 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[N:4]=[C:3]1[C:14]1[CH:28]=[CH:27][C:17]([CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:16][CH:15]=1.[C:29]([OH:32])(=O)[CH3:30]>N1C=CC=CC=1>[Cl:13][C:7]1[CH:6]=[C:5]2[C:10]([C:11](=[O:12])[N:2]([NH:1][C:29](=[O:32])[CH3:30])[CH:3]([C:14]3[CH:15]=[CH:16][C:17]([CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:27][CH:28]=3)[N:4]2[NH:2][C:11](=[O:12])[CH3:10])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18981114HCID 18981114, compound

Product 1

HCID 86753043HCID 86753043, compoundYield 123.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound obtained in Example 57 (3.0 g) and anhydrous acetic acid (2.2 g) were suspended in 20 ml of pyridine and refluxed at room temperature for 18 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was diluted with dichloromethane and washed with distilled water. The organic layer was dried over anhydrous magnesium sulfate and condensed under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane: methanol=50:1) and recrystallized from dichloromethane-n-hexane to provide 2.3 g of the desired compound as colorless crystals. Table 3 shows the chemical structure and property (melting point) of the compound obtained.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with distilled water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and condensed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane: methanol=50:1)
  7. customrecrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-24384eeaec0548edb51612d5f1cfe86d
Source dataset
uspto-grants-1998_08
Patent number
US05798344

Reaction notes

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