p-Bromobenzenesulfonyl chloride → HCID 9871189, compound

HRID 2301347Notes

Reaction equation

HRID 2301347 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:12]1[CH:20]=[CH:19][C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=1)=[C:6]([OH:21])[C:5]2=[O:22].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[O:16]1[C:15]2[CH:19]=[CH:20][C:12]([C:7]3[O:8][C:9]4[C:4]([C:5](=[O:22])[C:6]=3[OH:21])=[CH:3][C:2]([NH:1][S:30]([C:27]3[CH:28]=[CH:29][C:24]([Br:23])=[CH:25][CH:26]=3)(=[O:32])=[O:31])=[CH:11][CH:10]=4)=[CH:13][C:14]=2[O:18][CH2:17]1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 99262072-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-amino-4H-1-benzopyran-4-one

Product 1

HCID 9871189HCID 9871189, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mg (336 pmol) of 6-amino-2-(benzo[1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one obtained in Example 24 was dissolved in 3 ml of pyridine, and the mixture was reacted with 2 molar equivalents of 4-bromobenzenesulfonylchloride at room temperature for 5 hours. After the reaction was completed, the product was diluted with 10 ml. of water, and the obtained solid was filtered. Then the resulting product was washed with water and ethylether, and dried to give 159 mg of the title compound in a yield of 91.6%.

Workup

  1. additionthe product was diluted with 10 ml
  2. filtrationof water, and the obtained solid was filtered
  3. washThen the resulting product was washed with water and ethylether
  4. customdried

Sources & evidence

ORD record
ord-0f7cca31131f4a7c93599cc7a6c90ef4
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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