Dimethyl Disulfide → HCID 22473636, compound

HRID 2183646Notes

Reaction equation

HRID 2183646 reaction equation
C([Li])CCC.[S:6]1[C:10]([C:11]2[N:12]3[CH2:18][CH2:17][N:16]=[C:13]3[S:14][CH:15]=2)=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2.[CH3:23][S:24]SC.[Cl-].[NH4+]>O1CCCC1>[S:6]1[C:10]([C:11]2[N:12]3[CH2:18][CH2:17][N:16]=[C:13]3[S:14][C:15]=2[S:24][CH3:23])=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 9943990HCID 9943990, compoundHCID 178418339Butyllithium

Product 1

HCID 22473636HCID 22473636, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

n-Butyllithium (2.5 M solution in hexanes; 4.0 ml) was added dropwise under nitrogen at −70° C. to a stirred solution of 3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole (2.58 g; prepared in a manner similar to that described in Example 15) in tetrahydrofuran (40 ml), then the mixture was stirred at −70° C. for 25 minutes. Dimethyl disulphide (0.9 ml) was added, the mixture was stirred at ambient temperature for 2 hours, then it was poured into saturated aqueous ammonium chloride solution (200 ml). The product was extracted into ethyl acetate (300 ml), then the extract was washed with water (200 ml) and saturated aqueous sodium chloride solution (2×100 ml), dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using a 19:1 mixture of ethyl acetate and methanol as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 3-(benzo[b]thiophen-2-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole (0.79 g) as a yellow solid, m.p. 95-97° C.

Workup

  1. customprepared in a manner similar to
  2. stirringthe mixture was stirred at ambient temperature for 2 hours
  3. extractionThe product was extracted into ethyl acetate (300 ml)
  4. washthe extract was washed with water (200 ml) and saturated aqueous sodium chloride solution (2×100 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvents were removed in vacuo
  7. customThe residue was purified by flash chromatography over silica using
  8. additiona 19:1 mixture of ethyl acetate and methanol as eluant
  9. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-59b9ebc274234bcab702a5a8d941e2a5
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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