Iodoethane → HCID 86719570, compound

HRID 2208901Notes

Reaction equation

HRID 2208901 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(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](I)[CH3:25]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:24][CH3:25])[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]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 70873932HCID 70873932, compound

Product 1

HCID 86719570HCID 86719570, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 DMF (10 mL), cesium carbonate (2.55 g, 7.82 mmol) and ethyl iodide (6.09 g, 39.1 mmol) were added. The resulting reaction mass was heated at 80° C. for 12 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 crude material which then used for next step as is (10 g, 91%).

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
  6. customto give crude material which

Sources & evidence

ORD record
ord-65aeaba2450b4ec8abe0188e8ecf5f4d
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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