Methyl iodide → HCID 178469908, compound

HRID 2054363Notes

Reaction equation

HRID 2054363 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:12][S:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469909HCID 178469909, compound

Product 1

HCID 178469908HCID 178469908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2-mercapto-4-imidazole carboxylate (II) (49.82 g, 289 mmol) and K2CO3 (79.92 g, 579 mmol) in DMF (1500 mL) was added MeI (18.55 mL, 298 mmol) at room temperature, with stirring. After 18 hrs, it was filtered. The filtrate was concentrated under high vacuum to remove DMF. The residue was then filtered through a silica gel pad with EtOAc, and concentrated. PhMe (200 mL) was then added, followed by addition of Hexanes (1000 mL), precipitating III (50.5 g, 94%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): 7.69 (s, 1H), 4.35 (q, J=7.1 Hz, 2H), 2.67 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationit was filtered
  2. concentrationThe filtrate was concentrated under high vacuum
  3. customto remove DMF
  4. filtrationThe residue was then filtered through a silica gel pad with EtOAc
  5. concentrationconcentrated
  6. additionPhMe (200 mL) was then added
  7. additionfollowed by addition of Hexanes (1000 mL)
  8. customprecipitating III (50.5 g, 94%) as a yellow solid

Sources & evidence

ORD record
ord-e62f5e7ddb4c4dc7a990d8dc589b74cd
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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