m-Chloroperbenzoic acid → HCID 22558451, compound

HRID 984440Notes

Reaction equation

HRID 984440 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:25][C:26](=[O:40])[C:27]([NH:29][C:30]([CH3:39])([CH3:38])[CH2:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[O:28])[CH:17]=[CH:18][C:19]=1[C:20]1[O:24][CH:23]=[N:22][CH:21]=1>ClCCl.C(OCC)(=O)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:25][C:26](=[O:40])[C:27]([NH:29][C:30]([CH3:38])([CH3:39])[CH2:31][C:32]2[CH:33]=[CH:34][N+:35]([O-:6])=[CH:36][CH:37]=2)=[O:28])[CH:17]=[CH:18][C:19]=1[C:20]1[O:24][CH:23]=[N:22][CH:21]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22558416HCID 22558416, compound

Product 1

HCID 22558451HCID 22558451, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

30 mg (0.1 mmol) of 60% 3-chloroperoxybenzoic acid were added to a stirred solution of 20 mg (0.051 mmol) of N-[3-methoxy-4-(5-oxazolyl)phenyl]-N′-[1,1-dimethyl-2-(4-pyridyl)ethyl]oxalamide in 1 ml of dichloromethane. The mixture was stirred for 1 hour then diluted with ethyl acetate, washed with sodium bisulphite solution, sodium bicarbonate solution and brine. The organic solution was dried over magnesium sulphate, evaporated to dryness and the residue triturated with diethyl ether to give 13 mg of N-[3-methoxy-4-(5-oxazolyl)phenyl]-N′-[1,1-dimethyl-2-(1-oxido-4-pyridyl)ethyl]oxalamide as an off-white solid. MS: m/e 411 [M+]+.

Workup

  1. washwashed with sodium bisulphite solution, sodium bicarbonate solution and brine
  2. dry with materialThe organic solution was dried over magnesium sulphate
  3. customevaporated to dryness
  4. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-862d4a1ece874a778fbfa68f373d640f
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

Loading…