Dichloromethane → HCID 23114552, compound

HRID 2080487Notes

Reaction equation

HRID 2080487 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[C:6]([CH:16]([S:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:7][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[N:9][CH:10]=1.ClC1C=CC=C(C(OO)=[O:41])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.CCCCCC>[Cl:4][C:5]1[C:6]([CH:16]([S:25]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[O:41])[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:7][C:8]([NH:11][S:12]([CH3:15])(=[O:13])=[O:14])=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 23114712HCID 23114712, compound

Product 1

HCID 23114552HCID 23114552, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a methylene chloride (10 ml) solution of N-[5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanesulfonamide (331 mg, 0.696 mmol) was added 3-chloroperbenzoic acid (120 mg, 0.696 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. At the same temperature, 3-chloroperbenzoic acid (60 mg, 0.348 mmol) was added to the reaction mixture. After stirring at 0° C. for 10 minutes, a saturated aqueous solution of sodium thiosulfate was added to the reaction mixture. The resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure. To the residue thus obtained was added ether and the solid thus precipitated was collected by filtration to give the title compound (281 mg, 0.572 mmol, 82%) as a white powder.

Workup

  1. stirringAfter stirring at 0° C. for 10 minutes
  2. extractionThe resulting mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure
  8. customTo the residue thus obtained
  9. customthe solid thus precipitated
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d118dd87dbe3479d9aafbc766b6ea752
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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