Iodoethane → HCID 70913567, compound

HRID 2208903Notes

Reaction equation

HRID 2208903 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]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]([CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]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 70873958HCID 70873958, compound

Product 1

HCID 70913567HCID 70913567, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-3-((cyclopentylmethyl)amino)-2-methylbenzoate (1.0 g, 3.54 mmol) in DMF (10 mL), cesium carbonate (2.31 g, 7.09 mmol) and ethyl iodide (5.53 g, 35.4 mmol) were added. The resulting reaction mass was heated at 80° C. for 12 h. The mixture was cooled to room temperature and filtered. The residue was washed with ethyl acetate and the filtrate was concentrated to a residue which was purified by column chromatography to afford the title compound (1.0 g, 91%).

Workup

  1. customThe resulting reaction mass
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe residue was washed with ethyl acetate
  5. concentrationthe filtrate was concentrated to a residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f0bb76e94571442697bc875b89368f75
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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