Dimethyl Disulfide → HCID 22473890, compound

HRID 2183672Notes

Reaction equation

HRID 2183672 reaction equation
Br.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]=[C:8]([C:11]3[N:12]4[CH2:19][CH2:18][N:17]=[C:13]4[S:14][C:15]=3Br)[CH:9]=[CH:10][C:3]1=2.C([Mg]Cl)C.[CH3:24][S:25]SC>O1CCCC1>[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]=[C:8]([C:11]3[N:12]4[CH2:19][CH2:18][N:17]=[C:13]4[S:14][C:15]=3[S:25][CH3:24])[CH:9]=[CH:10][C:3]1=2

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 22474068HCID 22474068, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 22473890HCID 22473890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(Benzo[b]thiophen-5-yl)-2-bromo-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (0.4 g; prepared as described in Example 28) was added in portions under nitrogen at 0-5° C. over 8 minutes to a stirred solution of ethylmagnesium chloride (2M solution in ether; 1.4 ml) in tetrahydrofuran (10 ml), then the mixture was stirred at 0° C. for 20 minutes and at ambient temperature for 1.25 hours. Dimethyl disulphide (0.14 ml) was added at 0-5° C., the mixture was stirred at this temperature for 10 minutes and at ambient temperature for 4.5 hours, then it was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (20 ml). The product was extracted into ethyl acetate (30 ml+2×25 ml), the combined extracts were washed with water (2×25 ml) and saturated aqueous sodium chloride solution (25 ml), then they were dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using a 9:1 mixture of ethyl acetate and methanol as eluant. Appropriate fractions were combined and the solvents were removed in vacuo to give 3-(benzo[b]thiophen-5-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole (2 mg) as a yellow solid, 1H-nmr (DMSO-d6): δH 2.25 (3H, s, —SCH3), 3.68-4.19 (4H, m, —CH2CH2—), 7.36 (1H, d, J 1.7 Hz, ArH), 7.39-7.41 (1H, m, ArH), 7.54 (1H, d, J 5.45 Hz, ArH), 7.87 (1H, d, J 1.4 Hz, ArH), 7.96 (1H, d, J 8.3 Hz, ArH).

Workup

  1. stirringthe mixture was stirred at this temperature for 10 minutes and at ambient temperature for 4.5 hours
  2. customit was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (20 ml)
  3. extractionThe product was extracted into ethyl acetate (30 ml+2×25 ml)
  4. washthe combined extracts were washed with water (2×25 ml) and saturated aqueous sodium chloride solution (25 ml)
  5. dry with materialthey were dried (MgSO4)
  6. customthe solvents were removed in vacuo
  7. customThe residue was purified by flash chromatography over silica using
  8. additiona 9:1 mixture of ethyl acetate and methanol as eluant
  9. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-4452d718f3ca49eaa6d0c325f74af178
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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