Dimethylformamide → N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamide

HRID 403651Notes

Reaction equation

HRID 403651 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH3:26][O:27][CH2:28][CH2:29]Br>COCCBr.O>[CH3:26][O:27][CH2:28][CH2:29][O:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamide

Product 1

HCID 67287383N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamideYield 81.2%

Reagents, catalysts & solvents 2

HCID 809722-Bromoethyl methyl etherCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of N-(2-hydroxy-4-nitrophenyl)acetamide (93 g, 0.47 mol, 1.00 equiv), potassium carbonate (184 g, 1.33 mol, 2.81 equiv) and dimethylformamide (465 ml) was stirred at 60° C. as 2-bromoethyl methyl ether (90 g, 0.647 mol, 1.36 equiv) was added over 15 minutes. After 1 hour, additional 2-bromoethyl methyl ether (4 g, 0.028 mol, 0.059 equiv) was added and the mixture was stirred at 60° C. for another hour. The mixture was cooled to room temperature and poured into 1 L of water. After 30 minutes, the product was formed and collected by filtration and washed with water and heptane. The product was dried in a vacuum oven at 60° C. to give the title compound 97 g. MS (ESI) m/z: 255 (M+1).

Workup

  1. additionwas added over 15 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. waitAfter 30 minutes
  4. customthe product was formed
  5. filtrationcollected by filtration
  6. washwashed with water and heptane
  7. customThe product was dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-f8d5e112cadd45778c28de7b596a7089
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Reaction notes

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