m-Chloroperbenzoic acid → HCID 13606757, compound

HRID 1380104Notes

Reaction equation

HRID 1380104 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][CH3:19])[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]([CH3:25])[NH:8][C:7]=1[CH3:26])=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[CH3:26][C:7]1[NH:8][C:9]([CH3:25])=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18]([CH3:19])=[O:35])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13755647HCID 13755647, compound

Product 1

HCID 13606757HCID 13606757, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.092 g (2.91 mm) of diethyl-2,6-dimethyl-4-(2-methylthiophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 33 in 35 mL of dry CH2Cl2 was stirred at -78° C. under Ar and treated with 650 mg (3.20 mm) of m-chloroperbenzoic acid. After 1 hour the reaction was diluted with CH2Cl2 (150 mL) and washed with 10% aqueous sodium thiosulfate, H2O, and brine, dried (anhydrous MgSO4), filtered and concentrated to give 1.10 g of crude sulfoxide 34 (100%) used without purification for the following step.

Workup

  1. washwashed with 10% aqueous sodium thiosulfate, H2O, and brine
  2. dry with materialdried (anhydrous MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb76085206524bb4bdcbc7b071539507
Source dataset
uspto-grants-1986_04
Patent number
US04579851

Reaction notes

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