m-Chloroperbenzoic acid → 6,7-Dichloro-2-isopropyl-3-(5-methyl-1,3,4-thiadiazol-2-ylsulfinyl)quinoxaline

HRID 584650Notes

Reaction equation

HRID 584650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([CH:13]([CH3:15])[CH3:14])[C:6]([S:16][C:17]1[S:18][C:19]([CH3:22])=[N:20][N:21]=1)=[N:5]2.C1C=C(Cl)C=C(C(OO)=[O:31])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([CH:13]([CH3:14])[CH3:15])[C:6]([S:16]([C:17]1[S:18][C:19]([CH3:22])=[N:20][N:21]=1)=[O:31])=[N:5]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 98642016,7-Dichloro-2-isopropyl-3-(5-methyl-1,3,4-thiadiazol-2-ylsulfanyl)quinoxaline

Product 1

HCID 99082496,7-Dichloro-2-isopropyl-3-(5-methyl-1,3,4-thiadiazol-2-ylsulfinyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6,7-dichloro-2-isopropyl-3-(5-methyl-1,3,4-thiadiazol-2-ylsulfanyl)quinoxaline (168 mg, 0.45 mmol) prepared as described in example 1 in dichloromethane (6 ml) was stirred in a dry ice/acetone bath at −78° C. while mCPBA (142 mg, 0.45 mmol) was added. After 8.5 hours, the reaction was quenched by addition of a saturated solution of sodium bi-carbonate. The layers were separated and the aqueous layer was extracted twice with chloroform. Evaporation of the solvent yielded a pale yellow solid. The product was purified by flash column chromatography using ethyl acetate:hexanes 1:3 to afford the title compound.

Workup

  1. additionwas added
  2. customthe reaction was quenched by addition of a saturated solution of sodium bi-carbonate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice with chloroform
  5. customEvaporation of the solvent
  6. customyielded a pale yellow solid
  7. customThe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-9f6af45114c243f987e4dd1376bc2a7a
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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