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Potassium Iodide → HCID 14722394, compound

HRID 1031721
Notes
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Reaction equation

HRID 1031721 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:5]=2[O:4][CH:3]=1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu].C(OCC)(=O)C.O>[CH3:17][S:14]([NH:13][C:11]1[C:10]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:9][C:6]2[C:7](=[O:8])[C:2]([NH:1][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:3][O:4][C:5]=2[CH:12]=1)(=[O:15])=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 10783765HCID 10783765, compound

Product 1

HCID 14722394HCID 14722394, compoundYield 10.2%

Reagents, catalysts & solvents 4

HCID 23978
Copper
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

3.46 g of 3-amino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one was dissolved in 35 ml of N,N-dimethylformamide. Thereto were added 7 ml of bromobenzene, 1.66 g of potassium iodide, 1.38 g of potassium carbonate and 0.64 g of a copper powder. The mixture was refluxed for 6 hours. The reaction mixture was introduced into a mixture consisting of 300 ml of water and 200 ml of ethyl acetate. The insolubles were removed by filtration, and the filtrate was adjusted to pH 4 with 4N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 20:1 mixture of toluene and ethyl acetate) and then recrystallized from acetonitrile to obtain 430 mg (yield: 10.2%) of 7-methylsulfonylamino-3-phenylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 212°-213° C.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. additionThe reaction mixture was introduced into a mixture
  3. customThe insolubles were removed by filtration
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by a column chromatography (eluant
  9. additiona 20:1 mixture of toluene and ethyl acetate) and
  10. customthen recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4a6cba48849c4b749532dcac4aa33dc9
Source dataset
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04954518

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes