Dimethyl Disulfide → HCID 10268863, compound

HRID 2183674Notes

Reaction equation

HRID 2183674 reaction equation
Br.[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([C:11]3[N:12]4[CH2:19][CH2:18][N:17]=[C:13]4[S:14][C:15]=3Br)=[CH:8][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[C:7]([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:8][CH:9]=[CH:10][C:3]1=2

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 22473769HCID 22473769, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 10268863HCID 10268863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

3-(Benzo[b]thiophen-4-yl)-2-bromo-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (15 g; prepared in a manner similar to that described in Example 22) was added in portions under nitrogen at 0-5° C. over 20 minutes to a stirred solution of ethylmagnesium chloride (2M solution in ether; 45 ml) in tetrahydrofuran (225 ml), then the mixture was stirred at 0-5° C. for 2 hours. The mixture was cooled to 0° C. and dimethyl disulphide (5.4 ml) was added, then the mixture was stirred at ambient temperature for 18 hours and quenched by the addition of saturated aqueous ammonium chloride solution (150 ml). The majority of the tetrahydrofuran was removed in vacuo, the residue was diluted with water (200 ml) and the product was extracted into ethyl acetate (400 ml). The extract was washed with water (300 ml) and saturated aqueous sodium chloride solution (2×150 ml), then it was dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified by Biotage flash chromatography over silica using a 96:4 mixture of ethyl acetate and methanol as eluant. Appropriate fractions were combined and the solvents removed in vacuo to leave 3-(benzo[b]thiophen-4-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole (7.3 g) as a pale yellow solid, m.p. 104-107° C.

Workup

  1. customprepared in a manner similar to
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringthe mixture was stirred at ambient temperature for 18 hours
  4. customquenched by the addition of saturated aqueous ammonium chloride solution (150 ml)
  5. customThe majority of the tetrahydrofuran was removed in vacuo
  6. additionthe residue was diluted with water (200 ml)
  7. extractionthe product was extracted into ethyl acetate (400 ml)
  8. washThe extract was washed with water (300 ml) and saturated aqueous sodium chloride solution (2×150 ml)
  9. dry with materialit was dried (Na2SO4)
  10. customthe solvents were removed in vacuo
  11. customThe residue was purified by Biotage flash chromatography over silica using
  12. additiona 96:4 mixture of ethyl acetate and methanol as eluant
  13. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-ca9765a5c81544aa86c45c3248272574
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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