m-Chloroperbenzoic acid → HCID 19824174, compound

HRID 728334Notes

Reaction equation

HRID 728334 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:24])([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[CH2:10][C:11](=[O:17])[NH:12][CH2:13][CH2:14][S:15][CH3:16].ClC1C=CC=C(C(OO)=[O:33])C=1>C(O)(C)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:24])([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[CH2:10][C:11](=[O:17])[NH:12][CH2:13][CH2:14][S:15]([CH3:16])=[O:33]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19824171HCID 19824171, compound

Product 1

HCID 19824174HCID 19824174, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-(2,4-Dichlorophenyl)-1-[N-(2-[methylthio]ethyl)carbamoyl]-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.8 g) and m-chloroperbenzoic acid (85%, 0.35 g, 1 equiv.) were stirred at room temperature in a mixture of isopropanol and methylene chloride (1:1, v/v, 40 ml) for two days. The solvents were then removed under reduced pressure, and the residue was chromatographed on silica (Merck, "Kieselgel 60 ", 25 g), eluting with a mixture of chloroform, methanol and ammonia (sp. gr. 0.880) (160:20:5, v/v). A portion of the isomer which was eluted first was obtained pure, 116 mg, m.p. 168°-170° C.

Workup

  1. customThe solvents were then removed under reduced pressure
  2. customthe residue was chromatographed on silica (Merck, "Kieselgel 60 ", 25 g)
  3. washeluting with a mixture of chloroform, methanol and ammonia (sp. gr. 0.880) (160:20:5
  4. washA portion of the isomer which was eluted first
  5. customwas obtained pure

Sources & evidence

ORD record
ord-cb9e0459dbe8414f8c34abd2020399e7
Source dataset
uspto-grants-1991_09
Patent number
US05047548

Reaction notes

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