m-Chloroperbenzoic acid → 5-chloro-N-(2-oxiranylmethyl)-2-thiophenecarboxamide

HRID 68471Notes

Reaction equation

HRID 68471 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[S:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:21])C=1>ClCCl>[Cl:12][C:9]1[S:8][C:7]([C:5]([NH:4][CH2:1][CH:2]2[CH2:3][O:21]2)=[O:6])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21919842N-allyl-5-chlorothiophenecarboxamide

Product 1

HCID 219197985-chloro-N-(2-oxiranylmethyl)-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cooled solution of 2.0 g (9.92 mmol) of N-allyl-5-chloro-2-thiophenecarboxamide in 10 ml of dichloromethane is admixed with metachloroperbenzoic acid (183 g, about 60% strength). The mixture is stirred overnight, during which it is allowed to warm to room temperature, and is then washed with 10% sodium hydrogen sulphate solution (three times). The organic phase is washed with saturated sodium bicarbonate solution (twice) and with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The product is purified by silica gel chromatography (cyclohexane/ethyl acetate 1:1).

Workup

  1. washis then washed with 10% sodium hydrogen sulphate solution (three times)
  2. washThe organic phase is washed with saturated sodium bicarbonate solution (twice) and with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe product is purified by silica gel chromatography (cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-9907e1226d07439c8efd97717889ab65
Source dataset
uspto-grants-2014_09
Patent number
US08822458B2

Reaction notes

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