Methyl iodide → HCID 86719538, compound

HRID 2208705Notes

Reaction equation

HRID 2208705 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][C:9]([Cl:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:19](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Cl:1][C:2]1[C:11]([N:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[CH3:19])=[CH:10][C:9]([Cl:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70873980HCID 70873980, compound

Product 1

HCID 86719538HCID 86719538, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 2,5-dichloro-3-(cyclopentylamino)benzoate (0.275 g, 0.958 mmol) in acetonitrile (5 mL) was added cesium carbonate (0.622 g, 1.9 mmol) and methyl iodide (0.689 g, 4.78 mmol). The reaction mixture was heated at 80° C. for 18 h. On completion, the reaction was cooled to room temperature and filtered. The residue was washed with ethyl acetate and the filtrate was concentrated to afford methyl 2,5-dichloro-3-(cyclopentyl(methyl)amino)benzoate (0.27 g, 93%).

Workup

  1. temperatureOn completion, the reaction was cooled to room temperature
  2. filtrationfiltered
  3. washThe residue was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f32f99354d094932945f076342d0b2a7
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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