m-Chloroperbenzoic acid → HCID 19802752, compound

HRID 1645941Notes

Reaction equation

HRID 1645941 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:25]([O:27]C)=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[C:8]([S:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].ClC1C=C(C=CC=1)C(OO)=[O:45]>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:25]([OH:27])=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[C:8]([S:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[O:45])=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19802732HCID 19802732, compound

Product 1

HCID 19802752HCID 19802752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-butyl-4-[[4-[1-(carbomethoxy)-1-phenylmethoxy]phenyl]methyl]-5-(4-nitrobenzylthio)-4H-1,2,4-triazole (from Example 1, Step F) in dry CH2Cl2 is treated with m-chloroperoxybenzoic acid (1 equivalent), and the resulting mixture is stirred at room temperature for about 30 minutes or until TLC indicates complete reaction. At this point the mixture is partitioned between ethyl acetate and saturated NaHCO3 solution. The organic phase is washed repeatedly with saturated NaHCO3, then dried over MgSO4, filtered, and concentrated. The residue may be purified by chromatography on silica gel to give the title compound.

Workup

  1. customreaction
  2. customAt this point the mixture is partitioned between ethyl acetate and saturated NaHCO3 solution
  3. washThe organic phase is washed repeatedly with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue may be purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1bf8efe033964e068e0022520e8bba45
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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