m-Chloroperbenzoic acid → HCID 69223427, compound

HRID 900727Notes

Reaction equation

HRID 900727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:23])[CH2:10][S:11][C:12]2[NH:13][N:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[N:16]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:23])[CH2:10][S:11]([C:12]2[NH:13][N:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[N:16]=2)=[O:32])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178521525HCID 178521525, compound

Product 1

HCID 69223427HCID 69223427, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (2 mL) of N-(3-chloro-phenyl)-2-(5-pyridin-3-yl-2H-[1,2,4]triazol-3-ylsulfanyl)-acetamide (0.080 g, 0.25 mmol), m-chloroperbenzoic acid (0.25 mmol) was and the mixture was stirred for 2 h. The reaction mixture was quenched with sodium bicarbonate solution and the product extracted in ethyl acetate. The ethyl acetate layer was dried, filtered and evaporated to afford crude residue. This residue was purified by reverse phase HPLC to afford pure title compound (40 mg, 45%). MS (ES) 361.5

Workup

  1. customThe reaction mixture was quenched with sodium bicarbonate solution
  2. extractionthe product extracted in ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude residue
  7. customThis residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0afa07cf90e14ca9b4a79553a2d93c25
Source dataset
uspto-grants-2008_04
Patent number
US07361669B2

Reaction notes

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