Dimethylformamide → HCID 178504608, compound

HRID 2290019Notes

Reaction equation

HRID 2290019 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([S:21][CH3:22])=[CH:15][C:14]=3[F:23])=[O:9])=[CH:4][CH:3]=1.CN(C=[O:30])C.ClC1C=CC=C(C(OO)=O)C=1.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([S:21]([CH3:22])=[O:30])=[CH:15][C:14]=3[F:23])=[O:9])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 178503282HCID 178503282, compound

Product 1

HCID 178504608HCID 178504608, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 150 mg of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(methylsulfanyl)-3-quinolinecarboxamide from Example No. 170 and 0.75 mL of DMF in 15 mL of chloroform is treated with 79 mg of m-chloroperbenzoic acid. After stirring for 10 min the mixture is treated with 10 mL of a concentrated aqeous solution of sodium bisulfite. After stirring an addtional 5 min the phases are separated and the organic layer is washed with 15 mL of a saturated aqueous solution of sodium bicarbonate. The organic layer is dried (MgSO4) and the solvent was evaporated at reduced pressure. The residual solid is washed with a small volume of diethyl ether and dried to give 95 mg of a white solid.

Workup

  1. stirringAfter stirring an addtional 5 min the phases
  2. customare separated
  3. washthe organic layer is washed with 15 mL of a saturated aqueous solution of sodium bicarbonate
  4. dry with materialThe organic layer is dried (MgSO4)
  5. customthe solvent was evaporated at reduced pressure
  6. washThe residual solid is washed with a small volume of diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-6d2f27e6a03b4b7787cd19b51a50530d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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