Benzoyl chloride → HCID 54335804, compound

HRID 1856933Notes

Reaction equation

HRID 1856933 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>N1C=CC=CC=1>[C:22]([O:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 4834830HCID 4834830, compound

Product 1

HCID 54335804HCID 54335804, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 6-hydroxy-2-piperonylidene-3(2H)-benzofuranone 0.5 g was dissolved in pyridine 5 ml, benzoyl chloride 0.282 ml was added, and the mixture was refluxed for two hours. The reaction mixture was cooled to room temperature, ethyl acetate 50 ml was added, and the mixture was washed with 2N-hydrochloric acid 50 ml twice. The ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude extract was dissolved in ethyl acetate 10 ml and hexane 20 ml, and the precipitated crystals were dried over phosphorous pentoxide at a temperature of 60° C. for six hours under reduced pressure to obtain the desired compound 182.3 mg.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. washthe mixture was washed with 2N-hydrochloric acid 50 ml twice
  3. concentrationconcentrated under reduced pressure
  4. extractionThe crude extract
  5. dissolutionwas dissolved in ethyl acetate 10 ml
  6. dry with materialhexane 20 ml, and the precipitated crystals were dried over phosphorous pentoxide at a temperature of 60° C. for six hours under reduced pressure

Sources & evidence

ORD record
ord-dc6f5fca583b446c965c3a97f169ec1f
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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