Methanesulfonic Acid → HCID 20159238、化合物

HRID 236054

反応式

HRID 236054 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[CH3:9][S:10]([OH:13])(=[O:12])=[O:11].[CH2:14]1[S:16][CH2:15]1>CCOCC.O>[CH3:9][S:10]([O-:13])(=[O:12])=[O:11].[SH:16][CH2:15][CH2:14][N+:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

参加物

6

反応物 3

HCID 6395Methanesulfonic AcidHCID 79372,6-LutidineHCID 9865Thiirane

生成物 1

HCID 20159238HCID 20159238、化合物収率 19%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
25 °C

実験手順

A mixture of 2,6-dimethylpyridine (19.2 mL, 0.165 mol) and methanesulfonic acid (3.27 mL, 0.050 mol) was stirred for 15 min, treated with ethylene sulfide, (4.17 mL, 0.070 mol) and stirred at 100° C. for 42 h under a nitrogen atmosphere. After cooling to 25° C., the reaction mixture was diluted with ether (45 mL) and water (30 mL). The two layers were separated and the organic layer was extracted with water (2×5 mL). The aqueous layers were combined, filtered through a Celite pad, washed with ether (2×15 mL), pumped to remove the traces of organic solvents and poured on top of a column (3.0×12 cm) of μ-bondapak C-18. Elution with 3% acetonitrile 97% water mixture gave after lyophylization of the appropriate fractions 2.5 g of the impure title compound as a syrup. It was repurified by hplc (μ-bondapak C-18) to give 0.90 g (7%) of the title compound. ir (film) νmax : 2520 (SH), 1640 and 1625 (pyridinium), 1585, 1490, 1200 cm-1 (sulfonate), 1Hmr (DMSO-d6 +D2O) δ: 2.36 (3H, s, CH3SO3-), 4.62 (2H, m, CH2N+), 7.74 (2H, m, Pm of pyridinium), 8.24 (1H, m, Hp of pyridinium), uv (H2O) max : 272 (4080)mμ.

後処理

  1. stirringstirred at 100° C. for 42 h under a nitrogen atmosphere
  2. customThe two layers were separated
  3. extractionthe organic layer was extracted with water (2×5 mL)
  4. filtrationfiltered through a Celite pad
  5. washwashed with ether (2×15 mL)
  6. customto remove the traces of organic solvents
  7. additionpoured on top of a column (3.0×12 cm) of μ-bondapak C-18
  8. washElution with 3% acetonitrile 97% water mixture

出典と根拠

ORDレコード
ord-cb59d02486774fb5ab1b74aa7fd6b8e2
出典データセット
uspto-grants-1987_02
特許番号
US04642341

関連ノート

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