Iodoethane → 3-Amino-5-chloro-2-(2-ethoxybenzoyl)-benzofuran

HRID 450840Notes

Reaction equation

HRID 450840 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25].[CH2:27](I)[CH3:28]>CN(C=O)C.C(OCC)(=O)C>[NH2:7][C:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 587073613-Amino-5-chloro-2-(2-hydroxybenzoyl)-benzofuran

Product 1

HCID 587073663-Amino-5-chloro-2-(2-ethoxybenzoyl)-benzofuran

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of potassium carbonate (0.056 g, 0.4 mmol), 3-amino-5-chloro-2-(2-hydroxybenzoyl)-benzofuran (0.05 g, 0.4 mmol) and ethyl iodide (0.05 g, 0.34 mmol) in dry DMF is stirred at 60° C. for 2 h. The resulting mixture is diluted with ethyl acetate and washed with water. Drying over sodium sulfate, filtering, evaporating the solvent and purification of the residue by silicagel column chromatography yields the title compound, having a m.p. of 114-115° C.

Workup

  1. washwashed with water
  2. dry with materialDrying over sodium sulfate
  3. filtrationfiltering
  4. customevaporating
  5. customthe solvent and purification of the residue by silicagel column chromatography

Sources & evidence

ORD record
ord-16520b04eab941f4a7e5c566c4fd38a6
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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