tert-BUTYL CHLORIDE → (2E)-2-[2-(4-tert-butylphenoxy)phenyl]-2-methoxyimino-N-methylacetamide

HRID 1078480Notes

Reaction equation

HRID 1078480 reaction equation
[CH3:1][NH:2][C:3](=[O:21])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:5]/[O:6][CH3:7].[Cl-].[Al+3].[Cl-].[Cl-].[C:26](Cl)([CH3:29])([CH3:28])[CH3:27]>[N+](C)([O-])=O.O>[CH3:1][NH:2][C:3](=[O:21])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:16]=[CH:17][C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:19][CH:20]=1)=[N:5]/[O:6][CH3:7]

Participants

6

Reactant 3

HCID 10486tert-BUTYL CHLORIDEHCID 5483872(2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 76327444(2E)-2-[2-(4-tert-butylphenoxy)phenyl]-2-methoxyimino-N-methylacetamideYield 104.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6375NitromethaneSolvent

Procedure

To a solution of (E)-N-methyl-2-(2-phenoxyphenyl)2-methoxyiminoacetamide (300 mg) in nitromethane (3 ml), aluminium chloride (423 mg) and t-butyl chloride (147 mg) were added, followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with diethyl ether. The solvent was dried and evaporated, and the residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate to give 375 mg of the objective compound.

Workup

  1. extractionextracted with diethyl ether
  2. customThe solvent was dried
  3. customevaporated
  4. customthe residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-d9f7ce61bbf54e8087207362cccb1314
Source dataset
uspto-grants-1996_08
Patent number
US05548078

Reaction notes

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