1,3-Benzodioxole-5-carbonyl chloride → HCID 14049653, compound

HRID 466145Notes

Reaction equation

HRID 466145 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[Cl:13][C:14]1[C:15]([OH:21])=[CH:16][C:17](=[O:20])[NH:18][CH:19]=1>N1C=CC=CC=1>[Cl:13][C:14]1[C:15]([O:21][C:1](=[O:11])[C:2]2[CH:10]=[CH:9][C:8]3[O:7][CH2:6][O:5][C:4]=3[CH:3]=2)=[CH:16][C:17](=[O:20])[NH:18][CH:19]=1

Participants

4

Reactant 2

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 54679224Gimeracil

Product 1

HCID 14049653HCID 14049653, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3.80 g quantity of piperonyloyl chloride was added to a suspension of 2.00 g of 5-chloro-4-hydroxy-2-pyridone in 60 ml of pyridine, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was filtered and the filtrate was concentrated. The concentrate was washed successively with ethyl acetate, water and chloroform and then purified by silica gel column chromatography using as an eluent 2% methanol-chloroform, thereby producing 200 mg of the title compound in a yield of 5%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe concentrate was washed successively with ethyl acetate, water and chloroform
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b271c98846ae43d5a9f1172f7c6e8e77
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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