Iodoethane → HCID 86719549, compound

HRID 2208769Notes

Reaction equation

HRID 2208769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[C:20](=O)([O-])[O-].[Cs+].[Cs+].[CH2:26](I)[CH3:27]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:26][CH3:27])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:20])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 86719550HCID 86719550, compound

Product 1

HCID 86719549HCID 86719549, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-chloro-3-(cycloheptylamino)-2-methylbenzoate (0.8 g, 2.70 mmol) in dry DMF (10 mL), cesium carbonate (1.76 g, 5.4 mmol) and ethyl iodide (2.11 g, 13.5 mmol) were added and the resulting reaction mixture heated at 80° C. for 18 h. On completion, the mixture was cooled to room temperature and filtered, the residue washed with ethyl acetate and the filtrate concentrated before purification by column chromatography to afford the desired methyl 5-chloro-3-(cycloheptyl(ethyl)amino)-2-methylbenzoate (0.220 g, 25%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureOn completion, the mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthe residue washed with ethyl acetate
  5. concentrationthe filtrate concentrated before purification by column chromatography

Sources & evidence

ORD record
ord-44f5932e58734d69a598f6eeb4d6ac2b
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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