m-Chloroperbenzoic acid → 3-(Methanesulfinyl)-4-methyl-5-(naphthalen-2-yl)-4H-1,2,4-triazole

HRID 1199384Notes

Reaction equation

HRID 1199384 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[N:5][N:4]=[C:3]1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)Cl>[CH3:1][N:2]1[C:6]([S:7]([CH3:8])=[O:24])=[N:5][N:4]=[C:3]1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 30879994H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-naphthalenyl)-

Product 1

HCID 30880023-(Methanesulfinyl)-4-methyl-5-(naphthalen-2-yl)-4H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, 0° C., solution of 4-methyl-5-methylthio-3-(2-naphthyl)-4H-1,2,4-triazole (4.00 g, 1.57×10-2 mole) and CH2Cl2 (110 ml) was added portionwise m-chloroperoxybenzoic acid (3.38 g, 1.57×10-2 mole). After stirring overnight at room temperature the reaction was diluted with CH2Cl2 (200 ml), washed two times with saturated aqueous NaHCO3 and one time with saturated aqueous NaCl, and dried over anhydrous N2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving an off-white solid which was purified by flash chromatography (4% CH3OH/CH2Cl2). Crystallization from toluene afforded small colorless plates: 2.5 g (59%), mp 224°-226° C.

Workup

  1. washwashed two times with saturated aqueous NaHCO3 and one time with saturated aqueous NaCl
  2. customdried over anhydrous N2SO4
  3. customThe drying agent was removed by filtration
  4. customthe filtrate was evaporated at reduced pressure
  5. customleaving an off-white solid which
  6. customwas purified by flash chromatography (4% CH3OH/CH2Cl2)
  7. customCrystallization from toluene afforded small colorless plates

Sources & evidence

ORD record
ord-8a2f4328610949caa9f7c1331c985081
Source dataset
uspto-grants-1990_02
Patent number
US04900743

Reaction notes

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