m-Chloroperbenzoic acid → HCID 24826064, compound

HRID 910933Notes

Reaction equation

HRID 910933 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C1C=C(Cl)C=C(C(OO)=[O:29])C=1>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([S:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:29])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 24825874HCID 24825874, compound

Product 1

HCID 24826064HCID 24826064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL round bottom flask was charged with N-(4-methylthiazol-2-yl)-4-(phenylthio)pyridin-2-amine (0.050 g, 0.17 mmol) and dichloromethane (5 mL). The solution was cooled to 0° C., then MCPBA (0.029 g, 0.17 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. An additional 15 mg of MCPBA were added and the reaction mixture was stirred overnight. The reaction mixture was quenched with sodium bisulfite and extracted with dichloromethane. The organic layer was washed with a saturated solution of NaHCO3. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified using preparative TLC with 35% EtOAc in hexanes as the solvent system to afford 4-methyl-N-(4-(phenylsulfinyl)pyridin-2-yl)thiazol-2-amine as a light yellow solid. 1H NMR (CDCl3) δ 8.34 (d, 1H), 7.48-7.73 (m, 5H), 7.25 (s, 1H), 6.93 (dd, 1H), 6.41 (s, 1H), 2.36 (d, 3H); Mass spectrum (apci) m/z=316 (100) (M+H).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe reaction mixture was quenched with sodium bisulfite
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with a saturated solution of NaHCO3
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-5ecccd727016408f975c5bf78d45a887
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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