Methyl iodide → HCID 23449097, compound

HRID 989817Notes

Reaction equation

HRID 989817 reaction equation
[H-].[Na+].[CH:3]([NH:5][CH2:6][C:7]([C:9]1[N:10]=[CH:11][N:12]2[CH:16]=[CH:15][S:14][C:13]=12)=[O:8])=[O:4].CI.Cl[CH2:20]Cl>CN(C=O)C>[CH:3]([NH:5][CH:6]([CH3:20])[C:7]([C:9]1[N:10]=[CH:11][N:12]2[CH:16]=[CH:15][S:14][C:13]=12)=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 23449075HCID 23449075, compound

Product 1

HCID 23449097HCID 23449097, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (31 mg) was added to a solution of 0.24 g of 7-formylaminoacetylimidazo[5,1-b]thiazole in 4 ml of DMF. The mixture was stirred at 60° C. for 30 min, and cooled to room temperature. Thereafter, 176 mg of methyl iodide was added thereto. The mixture was stirred for one hr. Dichloromethane was added to the reaction mixture. The mixture was washed with water and saturated brine in that order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to give 0.12 g of 7-(2-formylaminopropionyl)imidazo[5,1-b]thiazole.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe mixture was stirred for one hr
  3. washThe mixture was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-76057f44c7b64c0aa82bb126c3edd431
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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