Iodoethane → HCID 70913248, compound

HRID 2208766Notes

Reaction equation

HRID 2208766 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:26](I)[CH3:27]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:26][CH3:27])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 70874136HCID 70874136, compound

Product 1

HCID 70913248HCID 70913248, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-3-(cyclohexylamino)-2-methylbenzoate (1.2 g, 4.3 mmol) in dry DMF (15 mL), cesium carbonate (2.78 g, 8.5 mmol) and ethyl iodide (3.35 g, 21.47 mmol) were added. The resulting reaction mixture was heated at 80° C. for 18 h. On completion, the reaction mixture was cooled to room temperature and filtered, and the residue washed with ethyl acetate. The filtrate was concentrated and purified by column chromatography to afford methyl 5-chloro-3-(cyclohexyl(ethyl)amino)-2-methylbenzoate (0.25 g, 22.7%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureOn completion, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthe residue washed with ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-4ee1408758074c54955952f0ef43ad42
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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