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

HRID 1271093Notes

Reaction equation

HRID 1271093 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-d46fb5af2e40471295de51925e8c9db5
Source dataset
uspto-grants-2007_04
Patent number
US07205303B2

Reaction notes

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