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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 1683218
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HRID 1683218 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine
용매
2회

실험 절차

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) δ 1.78 (quint, J=6.2 Hz, 4H), 2.41 (s, 6H), 2.43 (s, 6H), 2.97 (quart, J=6.6 Hz, 4H), 3.15 (t, J=6.6 Hz, 4H), 3.22 (s, 4H), 5.31 (t, J=6.5 Hz, 2H), 7.28 (d, J=8.3 Hz, 4H), 7.32 (d, J=8.3 Hz, 4H), 7.66 (d, J=8.3 Hz, 4H), 7.72 (d, J=8.3 Hz, 4H).

후처리

  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

출처 및 근거

ORD 기록
ord-45718aa4a8a24e6b8287fa4f543d8165
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05637578

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