Dimethylformamide → HCID 21848309, compound

HRID 618711Notes

Reaction equation

HRID 618711 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([NH2:13])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:14](Br)[CH3:15].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CC(C)=O>[CH2:14]([O:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([NH2:13])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 15434555HCID 15434555, compound

Product 1

HCID 21848309HCID 21848309, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1 g (5.64 mmol) of 4-hydroxybenzofuran-2-carboxamide, 0.5 ml (6.77 mmol) of ethyl bromide, 1.56 g (11.3 mmol) of potassium carbonate, 6 ml of anhydrous DMF and 50 ml of anhydrous acetone was heated at reflux over 24 hours. Subsequently, the mixture was poured on to 70 ml of ice-water, extracted twice with 100 ml of ethyl acetate each time and the combined organic phases were washed once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated in a vacuum. There were obtained 1.15 g (99%) of 4-ethoxybenzofuran-2-carboxamide as a yellow solid with m.p. 113°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux over 24 hours
  3. extractionextracted twice with 100 ml of ethyl acetate each time
  4. washthe combined organic phases were washed once with 100 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-914c0d572a274ffeb12c07a17fad0067
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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