p-Toluenesulfonic acid → 1-(2-Mercaptoethyl)-4-methylpyridinium p-toluenesulfonate

HRID 1583515

反応式

HRID 1583515 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[CH2:19]1[S:21][CH2:20]1>C1C=CC=CC=1.O.CCOCC>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[SH:21][CH2:20][CH2:19][N+:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1

参加物

7

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 79634-MethylpyridineHCID 9865Thiirane2 回

生成物 1

HCID 201592261-(2-Mercaptoethyl)-4-methylpyridinium p-toluenesulfonate収率 90%

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
23 °C

実験手順

To a suspension of p-toluenesulfonic acid (1.72 g, 0.01 mol) in benzene (6.5 mL) was added 4-picoline (1.17 mL, 0.012 mL). The resulting mixture was stirred under a nitrogen atmosphere at 23° C. for 30 min, treated with ethylenesulfide (0.65 mL, 0.011 mol) and stirred at 75° for 24 h. More ethylenesulfide (0.65 mL, 0.011 mol) was added and the stirring was continued at 75° C. for 24 h more. The reaction mixture was cooled to 23° C. and diluted with water (5 mL) and ether (8 mL). The aqueous layer was separated and washed with ether (3×8 mL). The traces of organic solvents were removed under vacuum and the compound was chromatographed on μ-bondapak C-18 with water as eluting solvent to give 2.94 g (90%) of the title compound as a colorless syrup; ir (film) νmax : 2510 (SH) 1640 (pyridinium), 1595, 1582, 1475, 1200 (sulfonate), 1031, 1010, 818 cm-1, 1Hmr (DMSO, d6) δ: 2.29 (3H, s, CH3 on pyridinium), 2.61 (s, CH3Ph), 2.4-2.8 (4H, SH, CH3Ph), 3.03 (2H, m[addition of D2O gave a t, J=6.4 Hz, at 3.04], CH2S), 4.68 (2H, t, J=6.4 Hz, CH2N+), 7.11, 7.49 (4H, 2d, J=7.9 Hz, Phenyl), 8.00 (2H, d, J=6.5 Hz, Hm of pyridinium), 8.89 (2H, d, J=6.5 Hz, Ho of pyridinium), uv (H2O) λmax : 256 (ε4315), 222 (ε17045) mμ.

後処理

  1. stirringstirred at 75° for 24 h
  2. waitthe stirring was continued at 75° C. for 24 h
  3. temperatureThe reaction mixture was cooled to 23° C.
  4. customThe aqueous layer was separated
  5. washwashed with ether (3×8 mL)
  6. customwere removed under vacuum
  7. customthe compound was chromatographed on μ-bondapak C-18 with water
  8. washas eluting solvent

出典と根拠

ORDレコード
ord-79337f39adc843529361f56bd35a55d7
出典データセット
uspto-grants-1985_11
特許番号
US04552696

関連ノート

読み込み中…