Potassium sulfite → HCID 59829843, compound

HRID 1947213Notes

Reaction equation

HRID 1947213 reaction equation
[CH:1]([C:4]1[C:5]([O:29][CH2:30][O:31][CH3:32])=[CH:6][C:7]([O:25][CH2:26][O:27][CH3:28])=[C:8]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:13](SC)=[N:12][N:11]=2)[CH:9]=1)([CH3:3])[CH3:2].Cl[C:34]1C=CC=C(C(OO)=O)C=1.[S:44]([O-:47])([O-])=[O:45].[K+].[K+]>C(Cl)Cl>[CH:1]([C:4]1[C:5]([O:29][CH2:30][O:31][CH3:32])=[CH:6][C:7]([O:25][CH2:26][O:27][CH3:28])=[C:8]([C:10]2[N:14]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[C:13]([S:44]([CH3:34])(=[O:47])=[O:45])=[N:12][N:11]=2)[CH:9]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24958Potassium sulfiteHCID 70297m-Chloroperbenzoic acidHCID 59829881HCID 59829881, compound

Product 1

HCID 59829843HCID 59829843, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-5-methylsulfanyl-4H-[1,2,4]triazole (F60-01: 2.87 g, 6.3 mmol) and methylene chloride (60 mL) were placed in a 200 mL eggplant shaped flask, cooled to 0° C., and methylene chloride solution of metachloroperbenzoic acid (3.77 g, 21.9 mmol) was gradually added in 4 portions, and the mixture was stirred for 9.5 hours. After completing the reaction, 10% aqueous potassium sulfite (100 mL) was added and stirring was continued for 10 minutes. After that, the organic layer was extracted, washed twice with 1 N sodium hydroxide (50 mL), dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (F60-02: 2.67 g, 87%)

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 10 minutes
  4. extractionAfter that, the organic layer was extracted
  5. washwashed twice with 1 N sodium hydroxide (50 mL)
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-837ddfeab2ea4194a175330bdb8ddb02
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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