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

HRID 1199383Notes

Reaction equation

HRID 1199383 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[N:5][N:4]=[C:3]1[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.ClC1C=C(C=CC=1)C(OO)=[O:19]>C(Cl)Cl>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:3]1[N:2]([CH3:1])[C:6]([S:7]([CH3:8])=[O:19])=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6110894H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-thienyl)-

Product 1

HCID 30880013-(Methanesulfinyl)-4-methyl-5-(thiophen-2-yl)-4H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, 0° C., solution of 4-methyl-5-methylthio-3-(2-thienyl)-4H-1,2,4-triazole (4.85 g, 2.29×10-2 mole) and CH2Cl2 (170 ml) was added portionwise m-chloroperoxybenzoic acid (4.95 g, 2.29×10-2 mole). After stirring at room temperature overnight the reaction was 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 yielding an off-white solid which was purified by flash chromatography (40% acetone/EtOAc). Crystallization from EtOAc afforded small colorless plates: 2.78 g (53%), mp 105°-107° C.

Workup

  1. washwas washed 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. customyielding an off-white solid which
  6. customwas purified by flash chromatography (40% acetone/EtOAc)
  7. customCrystallization from EtOAc afforded small colorless plates

Sources & evidence

ORD record
ord-dc97481fa9ec4fe18d3199dc6192a7d2
Source dataset
uspto-grants-1990_02
Patent number
US04900743

Reaction notes

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