Dimethyl Disulfide → HCID 22473636、化合物

HRID 2183646ノート

反応式

HRID 2183646 の反応式
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

参加物

6

反応物 4

HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 9943990HCID 9943990、化合物HCID 178418339Butyllithium

生成物 1

HCID 22473636HCID 22473636、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-59b9ebc274234bcab702a5a8d941e2a5
出典データセット
uspto-grants-2005_05
特許番号
US06900216B2

反応ノート

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