Methyl iodide → HCID 86719572, compound

HRID 2208905Notes

Reaction equation

HRID 2208905 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[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:18](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:17][CH2:16][CH2:15]2)[CH3:18])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70874019HCID 70874019, compound

Product 1

HCID 86719572HCID 86719572, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-3-(cyclobutylamino)-2-methylbenzoate (0.7 g, 2.8 mmol) in acetonitrile-(10 mL), cesium carbonate (2.2 g, 6.8 mmol) and methyl iodide (3.9 g, 28 mmol) were added. The resulting reaction mass was heated at 80° C. for 8 h. On completion, the reaction mass was cooled to room temperature and filtered. The residue was washed with ethyl acetate and the filtrate was concentrated to give the title compound (0.62 g, 84%).

Workup

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

Sources & evidence

ORD record
ord-1975a6d074194f91a4ba903cda06341f
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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