m-Chloroperbenzoic acid → HCID 19041120, compound

HRID 1683797Notes

Reaction equation

HRID 1683797 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:24]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[N:28]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH3:23])[CH3:13].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:24]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N+:30]=3[O-:9])[N:28]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH3:23])[CH3:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19041094HCID 19041094, compound

Product 1

HCID 19041120HCID 19041120, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 38.5 g of metachloroperbenzoic acid (80%) dissolved in 400 ml of methylene chloride was dropwise added, with ice cooling, to a solution of 49.6 g of 2-(3,4-diethoxyphenyl)-4-(2-pyridyl)thiazole dissolved in 250 ml of methylene chloride. The mixture was stirred at room temperature for 2 hours. To the reaction mixture was added an aqueous sodium hydrogencarbonate solution, followed by separation of layers. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was recrystallized from ethyl acetate to obtain 45.2 g of 2-[2-(3,4-diethoxyphenyl)-4-thiazolyl]pyridine-1-oxide.

Workup

  1. customfollowed by separation of layers
  2. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e4d559bfae9d453ea17632fa1801dcc6
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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