Dimethylformamide → Ace-011

HRID 748623Notes

Reaction equation

HRID 748623 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:26](Br)[CH3:27]>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH2:26][CH3:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl Bromide2×HCID 11430Potassium CarbonateHCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamide

Product 1

HCID 2877953Ace-011Yield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 400 g of 2-acetamido-5-nitrophenol in a 12-L, 4-necked flask equipped with a reflux condenser, nitrogen inlet, thermocouple, addition funnel, and mechanical stirrer was added 790 g of potassium carbonate and 2.0 L of dimethylformamide. The mixture was stirred at 60° C. as 294 g of ethyl bromide was added over 30 minutes. After 1 hour, an additional 27 g of ethyl bromide was added and the mixture was stirred at 60° C. for another hour. The mixture was cooled to room temperature and poured into 4 L of water. After 30 minutes, the product was collected by filtration and washed with water and heptane. The product was dried in a vacuum oven at 60° C. to give 457 g of the title compound.

Workup

  1. additionthermocouple, addition funnel, and mechanical stirrer
  2. additionwas added over 30 minutes
  3. temperatureThe mixture was cooled to room temperature
  4. waitAfter 30 minutes
  5. filtrationthe product was collected 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-2b1b7385f7f6411ba627529b1292801d
Source dataset
uspto-grants-2008_07
Patent number
US07399865B2

Reaction notes

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