Sodium Thiosulfate → HCID 22936968, compound

HRID 853524Notes

Reaction equation

HRID 853524 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:25])=[CH:19][CH:18]=3)[CH:11]=2)=[CH:5][CH:4]=1.Cl[C:34]1C=CC=C(C(OO)=O)C=1.[S:44]([O-:48])([O-])(=[O:46])=S.[Na+].[Na+]>ClCCl.CCCCCC.C(OCC)(=O)C.O>[CH3:34][S:44]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:25])=[CH:19][CH:18]=3)[CH:11]=2)=[CH:7][CH:8]=1)(=[O:48])=[O:46]

Participants

8

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22936684HCID 22936684, compound

Product 1

HCID 22936968HCID 22936968, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

N-(4-(6-(4-Methylsulfanylphenylamino)pyrimidin-4-yloxy)phenyl-N′-phenylurea (180 mg, 0.406 mmol) and 3-chloroperbenzoic acid (200 mg, 0.812 mmol) were stirred in dichloromethane (6 ml) at room temperature for 12 hours. A saturated aqueous sodium thiosulfate solution was added to suspend the reaction, and then the reaction solution was distributed between ethyl acetate and water, the organic layer was washed with 1N aqueous sodium hydroxide, water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=3:1), the fraction containing the target substance was concentrated and suspended in ethyl acetate, the suspension was diluted with hexane and the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (137 mg, 0.288 mmol, 71%) as colorless crystals.

Workup

  1. customthe reaction
  2. washthe organic layer was washed with 1N aqueous sodium hydroxide, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. distillationthe filtrate was distilled off under reduced pressure
  6. customThe obtained crude product
  7. additionthe fraction containing the target substance
  8. concentrationwas concentrated
  9. additionthe suspension was diluted with hexane
  10. filtrationthe crystals were filtered out
  11. washwashed with hexane
  12. customblow-dried

Sources & evidence

ORD record
ord-8b8322a7296b43ffaf41cb7d22187b30
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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