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Benzoyl chloride → N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-benzamide

HRID 2301349
Notes
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Reaction equation

HRID 2301349 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].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[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][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:11][CH:10]=4)=[CH:13][C:14]=2[O:18][CH2:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 99262072-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-amino-4H-1-benzopyran-4-one

Product 1

HCID 9887280N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-benzamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

30 mg (101 pmol) of 6-amino-2-(benzo[1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one obtained in Example 24 was dissolved in 2 ml of methylenechloride, and the mixture was reacted with 10 molar equivalents of benzoylchloride and excess amount of potassium carbonate at room temperature for 10 hours. The resulting product was filtered, washed with methylenechloride and water, and dried to give 32 mg of the title compound in a yield of 79%.

Workup

  1. filtrationThe resulting product was filtered
  2. washwashed with methylenechloride and water
  3. customdried

Sources & evidence

ORD record
ord-ecde7cfc742c4aba851587604ae0b00f
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06500846B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes