Diethyl Ether → HCID 22010989, compound

HRID 323124Notes

Reaction equation

HRID 323124 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:5])[CH3:2].[H-].[Na+].IC.[CH2:28](OCC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[N:8]([CH3:28])[C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 710786Ethyl 2-[(4-nitrobenzoyl)amino]benzoate

Product 1

HCID 22010989HCID 22010989, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-ethoxycarbonyl-N-(4-nitrobenzoyl)aniline (3.15 g) in N,N-dimethylformamide (30 ml) was added sodium hydride (60% in oil, 442 mg) and the solution was stirred at ambient temperature for 30 minutes. Iodomethane (1.56 g) was added to the solution and the mixture was stirred at ambient temperature for 4 hours. The solution was diluted with ethyl acetate and the solution was washed with successively with 1N hydrochloric acid, water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The oil was solidified with diethyl ether to give 2-ethoxycarbonyl-N-methyl-N-(4-nitrobenzoyl)aniline (3.28 g) as a pale yellow powder.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 4 hours
  2. washthe solution was washed with successively with 1N hydrochloric acid, water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil

Sources & evidence

ORD record
ord-f7f56115a7be464a920e62e418124d46
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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