Iodoethane → HCID 58679285, compound

HRID 1441754Notes

Reaction equation

HRID 1441754 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([NH2:14])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([NH:14][CH2:23][CH3:24])[CH:5]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 4026781methyl 3-amino-5-(trifluoromethyl)benzoate

Product 1

HCID 58679285HCID 58679285, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-amino-5-(trifluoromethyl)-benzoic acid methyl ester (J. Med. Chem. (1969) 12, 299-303; 4.23 g, 19.3 mmol), potassium carbonate (8.0 g, 57.9 mmol) and iodoethane (3.12 mL, 38.6 mmol) in 20 mL N,N-dimethylformamide is stirred at 65° C. for 14 hours in a tightly closed vessel. After cooling, the reaction mixture is filtered and the filtrate evaporated to dryness under reduced pressure. The residue is treated with water and extracted three times with ethyl acetate. The combined extracts are dried (Na2SO4) and the solvent is evaporated off under reduced pressure. The resulting residue is purified by column chromatography on silica gel, eluent hexane/methylene chloride (1:1).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. additionThe residue is treated with water
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined extracts are dried (Na2SO4)
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe resulting residue is purified by column chromatography on silica gel, eluent hexane/methylene chloride (1:1)

Sources & evidence

ORD record
ord-26abeaa345d84555ab58c242cc960bf9
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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