m-Chloroperbenzoic acid → 2-(4-([1,1'-Biphenyl]-4-ylmethoxy)phenyl)-N-(2-(dimethylnitroryl)ethyl)acetamide

HRID 1356464Notes

Reaction equation

HRID 1356464 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:38])C=1>CC(C)=O>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][CH2:19][CH2:20][N+:21]([CH3:23])([CH3:22])[O-:38])=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 99102684-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamide

Product 1

HCID 185083482-(4-([1,1'-Biphenyl]-4-ylmethoxy)phenyl)-N-(2-(dimethylnitroryl)ethyl)acetamideYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(4-([1,1′-biphenyl]-4-ylmethoxy)phenyl)-N-(2-(dimethylamino)ethyl)acetamide (0.2 g) in acetone (30 ml) was added m-chloroperbenzoic acid (0.2 g) and stirring was continued at room temperature for 18 hr. The reaction mixture was concentrated. The residue was recrystallized twice from ethyl acetate to obtain the titled compound (0.1 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-d61fc2194543486083946f31dba3c706
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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