Methyl iodide → HCID 86719569, compound

HRID 2208900Notes

Reaction equation

HRID 2208900 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])[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]([CH2:14][CH:15]([CH3:17])[CH3:16])[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 70873932HCID 70873932, compound

Product 1

HCID 86719569HCID 86719569, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-3-(isobutyl amino)-2-methylbenzoate (1.0 g, 3.9 mmol) in dry acetonitrile (10 mL), cesium carbonate (2.55 g, 7.8 mmol) and methyl iodide (5.55 g, 39 mmol) were added. The mixture was heated at 80° C. for 12 h. On completion, the mixture was cooled to room temperature and filtered. The residue was washed with ethyl acetate and the filtrate was concentrated to the title compound (1.0 g, 95%).

Workup

  1. temperatureOn completion, the mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe residue was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated to the title compound (1.0 g, 95%)

Sources & evidence

ORD record
ord-971dc88573bc447fbe4a53e50ab03c86
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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