Methyl iodide → HCID 178503574, compound

HRID 324478Notes

Reaction equation

HRID 324478 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[C:17](=[S:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:24]=1.[C:25](=O)(O)[O-].[Na+].CI>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[C:17]([S:23][CH3:25])=[N:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:24]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 516892Sodium BicarbonateHCID 88152155HCID 88152155, compound

Product 1

HCID 178503574HCID 178503574, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of the product from example 38, step (v) (1.8 g) in ethanol (200 ml) and sodium bicarbonate (0.5 g) in water (15 ml) was heated until a complete solution formed. After cooling to room temperature methyl iodide (0.33 ml) was added and the whole stirred for 18 h. Another aliquot of methyl iodide was added (0.2 ml) followed by heating at 50° C. for 4 h. The reaction mixture was concentrated under reduced pressure and then partitioned between dichloromethane and brine. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure to leave a beige foam. Purification was by chromatography eluting with ethyl acetate/methanol mixtures to give the subtitle product as colourless solid.

Workup

  1. temperaturewas heated until a complete solution
  2. customformed
  3. additionwas added
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. custompartitioned between dichloromethane and brine
  6. customThe organic phase was collected
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto leave a beige foam
  10. customPurification
  11. washeluting with ethyl acetate/methanol

Sources & evidence

ORD record
ord-ce7066069a78420da825cc22f47f2410
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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