Hydrogen Peroxide → 2-Ethylsulfinyl-5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazole

HRID 461685Notes

Reaction equation

HRID 461685 reaction equation
[CH2:1]([S:3][C:4]1[S:5][C:6]([C:9]([NH:11][CH2:12][CH2:13][CH:14]2[CH:18]3[CH2:19][CH2:20][CH:15]2[CH2:16][CH2:17]3)=[O:10])=[CH:7][N:8]=1)[CH3:2].[OH:21]O>C(O)(=O)C>[CH2:1]([S:3]([C:4]1[S:5][C:6]([C:9]([NH:11][CH2:12][CH2:13][CH:14]2[CH:18]3[CH2:19][CH2:20][CH:15]2[CH2:16][CH2:17]3)=[O:10])=[CH:7][N:8]=1)=[O:21])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 21391851HCID 21391851, compound

Product 1

HCID 213919872-Ethylsulfinyl-5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This example illustrates the preparation of the compounds of formula I wherein X is --SOR1. In this example a mixture of 20 g. of 2-ethylthio-5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazole (0.064 mole); 40 ml. of 30% aqueous hydrogen peroxide and 200 ml. of acetic acid is stirred at a temperature of from 40° to 50° C for 4 hours. The mixture is concentrated by evaporation of a large portion of the acetic acid, under vacuum, at room temperature (about 20° C) and the resulting residue poured into 500 ml. of ethyl acetate and then washed with aqueous sodium bicarbonate solution until no acetic acid is present in the organic layer. The ethyl acetate layer is then separated, dried with anhydrous magnesium sulfate, filtered, and the resulting filtrate evaporated to dryness, under vacuum, affording 2-ethylsulfinyl-5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazole.

Workup

  1. customthe preparation of the compounds of formula I wherein X
  2. concentrationThe mixture is concentrated by evaporation of a large portion of the acetic acid, under vacuum, at room temperature (about 20° C)
  3. additionthe resulting residue poured into 500 ml
  4. washof ethyl acetate and then washed with aqueous sodium bicarbonate solution until no acetic acid
  5. customThe ethyl acetate layer is then separated
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe resulting filtrate evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-39fc2a44343949c3a114932e3d96328e
Source dataset
uspto-grants-1977_12
Patent number
US04064135

Reaction notes

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