Sodium Chloride → HCID 23449279, compound

HRID 989824Notes

Reaction equation

HRID 989824 reaction equation
[CH3:1][S:2]([C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[CH:11][S:10][C:9]=12)(=[O:4])=[O:3].[CH3:13][Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.CI.[Cl-].[Na+]>C1COCC1>[CH2:1]([S:2]([C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[CH:11][S:10][C:9]=12)(=[O:3])=[O:4])[CH3:13]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 23448990HCID 23448990, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449279HCID 23449279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 725 mg of 7-methanesulfonylimidazo[5,1-b]thiazole in 35 ml of THF was cooled in an argon atmosphere to −70° C. A 1 N-lithiumbis(trimethylsilyl)amide/THF solution (3.9 ml) was added dropwise thereto at the same temperature. The mixture was stirred for 30 min. Thereafter, 0.25 ml of methyl iodide was added thereto. The mixture was stirred at the same temperature for 70 min. A saturated aqueous sodium chloride solution was added thereto, followed by extraction four times with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=9:1) to give 0.79 g of 7-ethanesulfonylimidazo[5,1-b]thiazole.

Workup

  1. stirringThe mixture was stirred at the same temperature for 70 min
  2. extractionfollowed by extraction four times with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-1ac339a8d0af41e5a4fa17fac7f677e9
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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