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Water → 4-methyl-N-[3-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[3-[(4-methylphenyl)sulfonylamino]propyl]amino]ethyl]amino]propyl]benzenesulfonamide

HRID 976182
ノート
印刷プレビュー

反応式

HRID 976182 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][NH:19][CH2:20][CH2:21][CH2:22][NH2:23].[OH2:24]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:23][CH2:22][CH2:21][CH2:20][N:19]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:18][CH2:17][N:16]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:15][CH2:14][CH2:13][NH:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:24])(=[O:9])=[O:8])=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 25378N,N'-bis(3-aminopropyl)ethylenediamine

生成物 1

HCID 30908484-methyl-N-[3-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[3-[(4-methylphenyl)sulfonylamino]propyl]amino]ethyl]amino]propyl]benzenesulfonamide収率 53%

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 (460 g, 2.41 mole) in pyridine (1.5 l) at 0° C. was added a solution of 1,5,8,12-tetraazadodecane (100 g, 0.574 mole) in pyridine (100 ml) under a dry argon atmosphere, maintaining the temperature ≤50° C. The addition required 1 h. The mixture was allowed to cool to room temperature and was stirred for 2 h. H2O (3 l) was slowly added to the cooled (ice bath) mixture. The resulting brown solid was filtered and washed thoroughly with H2O. The crude product was purified by recrystallization from DMF-H2O to give 238 g (53% yield) of the product as a crude granular solid: mp 141°-2° C.; 1H NMR (CDCl3) δ1.78 (quint, J=6.2 Hz, 4 H), 2.41 (s, 6 H), 2.43 (s, 6 H), 2.97 (quart, J=6.6 Hz, 4 H), 3.15 (t, J=6.6 Hz, 4 H), 3.22 (s, 4 H), 5.31 (t, J=6.5 Hz, 2 H), 7.28 (d, J=8.3 Hz, 4 H), 7.32 (d, J=8.3 Hz, 4 H), 7.66 (d, J=8.3 Hz, 4 H), 7.72 (d, J=8.3 Hz, 4 H).

後処理

  1. temperaturemaintaining the temperature ≤50° C
  2. additionThe addition required 1 h
  3. temperaturecooled (ice bath) mixture
  4. filtrationThe resulting brown solid was filtered
  5. washwashed thoroughly with H2O
  6. customThe crude product was purified by recrystallization from DMF-H2O

出典と根拠

ORDレコード
ord-7a704a149c3c4085ba874a10af8333f3
出典データセット
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05610293

反応ノート

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