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

HRID 2103441Notes

Reaction equation

HRID 2103441 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 meta-chloroperbenzoic acid (3.83 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-824012e940e74e388afd60bc3f9b242a
Source dataset
uspto-grants-2009_08
Patent number
US07576111B2

Reaction notes

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