Methyl iodide → HCID 70874150, compound

HRID 2208755Notes

Reaction equation

HRID 2208755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:23]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH3:23])[C:14]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86719545HCID 86719545, compound

Product 1

HCID 70874150HCID 70874150, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 5-chloro-3-(cyclopentanecarboxamido)-2-methylbenzoate (0.3 g, 1.01 mmol) in DMF, sodium hydride (0.060 g, 0.0015 mmol) was added at 0° C. and reaction mixture was allowed to stir for 15 min. Methyl iodide (0.32 mL, 0.50 mmol) was added and reaction mixture and was stirred at room temperature. After complete consumption of starting material, the reaction was quenched with addition of water and extracted with ethyl acetate. The combined organic layer was the washed with brine, dried (Na2SO4) and concentrated. The crude compound was used for the next step.

Workup

  1. customreaction mixture
  2. customreaction mixture
  3. stirringwas stirred at room temperature
  4. customAfter complete consumption of starting material
  5. customthe reaction was quenched with addition of water
  6. extractionextracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-243cfa0ae7184a2baff1c4d35cd66fa3
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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