m-Chloroperbenzoic acid → HCID 69892356, compound

HRID 2307264Notes

Reaction equation

HRID 2307264 reaction equation
[C:1]([N:9]1[CH2:13][CH:12]2[CH2:14][S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:11]2=[N:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[C:1]([N:9]1[CH2:13][CH:12]2[CH2:14][S:15](=[O:30])[CH:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[C:11]2[NH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22605764HCID 22605764, compound

Product 1

HCID 69892356HCID 69892356, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nicotinoyl-3,3a-dihydro-2H,4H-[1]-benzothiopyrano[4,3-c]pyrazole (6 g) synthesized in Example 37, dissolved in dichloromethane (50 ml) was added m-chloroperbenzoic acid (2.5 g, purity: 70%) with ice-cooling, to give rise to a reaction. After the completion of the reaction, the reaction mixture was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried and concentrated under vacuum. The residue was purified by silica gel column chromatography (methanol:chloroform=1/40) to obtain 2.3 g of a title compound (yield: 73%).

Workup

  1. temperaturecooling
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. washthe reaction mixture was washed with a saturated aqueous sodium bicarbonate solution
  6. customThe organic layer was dried
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1/40)

Sources & evidence

ORD record
ord-5051ac6bc5904a9b979258cecea22da7
Source dataset
uspto-grants-2004_12
Patent number
US06831083B2

Reaction notes

Loading…