m-Chloroperbenzoic acid → HCID 135833421, compound

HRID 247130Notes

Reaction equation

HRID 247130 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:35])=[C:5]([C:31]([O:33][CH3:34])=[O:32])[CH:6]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:7]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]=1.ClC1C=C(C=CC=1)C(OO)=[O:41].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]([CH3:35])=[C:5]([C:31]([O:33][CH3:34])=[O:32])[CH:6]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:7]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:41])[N:9]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 135833429HCID 135833429, compound

Product 1

HCID 135833421HCID 135833421, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.00 g of methyl 1,4-dihydro-2,6-dimethyl-3-(3-benzylthiomethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylate in 50 ml of chloroform was added 0.47 g of m-chloroperoxybenzoic acid. After the mixture was stirred at room temperature for 3 hours, the aqueous sodium bicarbonate was added and the stirring was continued for a while. The chloroform layer was separated, washed, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol (30:1) as eluent to give 980 mg of methyl 1,4-dihydro-2,6-dimethyl-3-(3-benzylsulfinylmethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylate, IR νmaxneat cm-1 : 3290, 3210, 1680, 1645, 1520, 1490, 1230.

Workup

  1. customThe chloroform layer was separated
  2. washwashed
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-afc665a4a01040b3a3008173ae110022
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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