Hydrogen Peroxide → 2-Ethylsulfinyl-5-(hex-5-ynylaminocarbonyl)thiazole

HRID 461929Notes

Reaction equation

HRID 461929 reaction equation
[CH2:1]([S:3][C:4]1[S:5][C:6]([C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])=[O:10])=[CH:7][N:8]=1)[CH3:2].[OH:18]O>C(O)(=O)C>[CH2:1]([S:3]([C:4]1[S:5][C:6]([C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])=[O:10])=[CH:7][N:8]=1)=[O:18])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 213926502-Ethylthio-5-(hex-5-ynylaminocarbonyl)thiazole

Product 1

HCID 213919462-Ethylsulfinyl-5-(hex-5-ynylaminocarbonyl)thiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In this preparation a mixture of 0.064 mole of 2-ethylthio-5-(hex-5-ynylaminocarbonyl) thiazole; 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-(hex-5-ynylaminocarbonyl)thiazole.

Workup

  1. customIn this preparation
  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-b21fbf5e239b4da08954b5beae29cc58
Source dataset
uspto-grants-1977_12
Patent number
US04064257

Reaction notes

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