m-Chloroperbenzoic acid → N-(4-methoxyphenyl)-2-oxiran-2-ylacetamide

HRID 230115Notes

Reaction equation

HRID 230115 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:14])[CH2:11][CH:12]=[CH2:13])=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:14])[CH2:11][CH:12]2[CH2:13][O:23]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18452750N-(4-methoxyphenyl)but-3-enamide

Product 1

HCID 58844915N-(4-methoxyphenyl)-2-oxiran-2-ylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of N-(4-methoxyphenyl)but-3-enamide (9) from the previous reaction was treated with m-chloroperbenzoic acid (2 eq.) and stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane, and washed with 1N sodium hydroxide. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to give crude N-(4-methoxyphenyl)-2-oxiran-2-ylacetamide, a compound of formula (10).

Workup

  1. washwashed with 1N sodium hydroxide
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-eef53b2d7396407cabf6e83b129ecf40
Source dataset
uspto-grants-2009_07
Patent number
US07566717B2

Reaction notes

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