S-Methyl methanethiosulfonate → 7-Methylthioimidazo[5,1-b]thiazole

HRID 989823Notes

Reaction equation

HRID 989823 reaction equation
C([Mg]Br)C.C1COCC1.I[C:11]1[N:12]=[CH:13][N:14]2[CH:18]=[CH:17][S:16][C:15]=12.[CH3:19][S:20]S(C)(=O)=O.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:19][S:20][C:11]1[N:12]=[CH:13][N:14]2[CH:18]=[CH:17][S:16][C:15]=12

Participants

7

Reactant 4

HCID 18064S-Methyl methanethiosulfonateHCID 25517Ammonium ChlorideHCID 177737777-Iodoimidazo[5,1-B]thiazoleHCID 178420660HCID 178420660, compound

Product 1

HCID 226315297-Methylthioimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1 M ethylmagnesium bromide/THF solution (1.4 ml) was added under ice cooling to a solution of 0.31 g of 7-iodoimidazo[5,1-b]thiazole in 3 ml of dry THF in an argon atmosphere. The mixture was stirred at the same temperature for one hr. Methyl methanethiolsulfonate (0.15 ml) was added thereto. The mixture was stirred at room temperature for 12 hr. A saturated aqueous ammonium chloride solution was added to the reaction solution. Ethyl acetate was added thereto. The mixture was washed with a dilute aqueous sodium thiosulfate solution and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate) to give 0.15 g of 7-methylthioimidazo[5,1-b]thiazole.

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hr
  2. washThe mixture was washed with a dilute aqueous sodium thiosulfate solution and saturated brine in that order
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-9d85925112e74f8287a00bdf46292787
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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