Sodium Hydroxide → 2-(4-Chlorophenyl)-6-(methylsulfonyl)benzo[d]thiazole

HRID 1886949Notes

Reaction equation

HRID 1886949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([S:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].[OH-:30].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([S:17]([CH3:18])(=[O:24])=[O:30])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 576174822-(4-Chlorophenyl)-6-(methylthio)benzo[d]thiazole

Product 1

HCID 673329402-(4-Chlorophenyl)-6-(methylsulfonyl)benzo[d]thiazoleYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-6-(methylthio)benzo[d]thiazole (240 mg, 0.82 mmol) in dichloromethane (20 mL) was added 3-chloroperoxybenzoic acid (77% in water, 710 mg, 4.11 mmol) over 5 min. The resulting mixture was stirred at room temperature for 3 h. 1M aqueous sodium hydroxide solution was added carefully, and the mixture was then stirred for 5 min. The organic layer was then washed with 1M aqueous sodium hydroxide solution, dried over anhydrous MgSO4 and evaporated. The resulting solid was recrystallised from hot ethyl acetate to afford 125 mg (47%) of the title compound (LCMS RT=6.81 min, MH+ 324.0)

Workup

  1. stirringthe mixture was then stirred for 5 min
  2. washThe organic layer was then washed with 1M aqueous sodium hydroxide solution
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was recrystallised from hot ethyl acetate

Sources & evidence

ORD record
ord-2fbe08e913f14b6584ff04b19fffae58
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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