Bis(3-aminopropyl)amine → Bis(3-{[(4-methylphenyl)sulfonyl]amino}propyl)[(4-methylphenyl)sulfonyl]amine

HRID 363386

反応式

HRID 363386 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][NH2:20]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:12][CH2:13][CH2:14][CH2:15][N:16]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][CH2:18][CH2:19][NH:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])(=[O:9])=[O:8])=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 5942Bis(3-aminopropyl)amineHCID 73974-Toluenesulfonyl chloride

生成物 1

HCID 373797Bis(3-{[(4-methylphenyl)sulfonyl]amino}propyl)[(4-methylphenyl)sulfonyl]amine収率 59%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

To a stirred solution of p-toluenesulfonyl chloride (240 g, 1.26 mole) in pyridine (600 ml) at 0° C. was added a solution of 1,5,9-triazanonane (50.0 g, 0.381 mole) in pyridine (100 ml) under a dry nitrogen atmosphere, maintaining the temperature ≤60° C. The addition required 15 minutes. The solvent was removed in vacuo and the resulting yellow oil was dissolved in ethyl acetate (1 l) and H2O (500 ml). The ethyl acetate layer was separated, washed with 0.1N HCl, H2O and saturated NaCl solution and dried (MgSO4). The solution was decolorized with silica gel and the solvent was removed in vacuo to give 133 g (59% yield) of the crude product as a glassy solid: 1H NMR (CDCl3) δ 1.71 (quint, J=6.6 Hz, 4 H), 2.42 (s, 6 H), 2.43 (s, 3 H), 2.96 (quart, J=6.4 Hz, 4 H), 3.11 (t, J=6.8 Hz, 4 H), 5.12 (t, J=6.6 Hz, 2 H), 7.30 (m, 6 H), 7.63 (m, 2 H), 7.73 (m, 4 H).

後処理

  1. temperaturemaintaining the temperature ≤60° C
  2. additionThe addition required 15 minutes
  3. customThe solvent was removed in vacuo
  4. dissolutionthe resulting yellow oil was dissolved in ethyl acetate (1 l)
  5. customThe ethyl acetate layer was separated
  6. washwashed with 0.1N HCl, H2O and saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-74d5eaa312b44262b58faba2559a5680
出典データセット
uspto-grants-1999_02
特許番号
US05874421

関連ノート

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