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Cyclohexylamine → N-Cyclohexyl-5-chloro-2-naphthalenesulfonamide

HRID 725777
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HRID 725777 반응식
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([S:19](Cl)(=[O:21])=[O:20])=[CH:14]2.C(N(C(C)C)CC)(C)C.ClC1C=CC=C2C=1C=CC=C2S(Cl)(=O)=O>C(Cl)(Cl)Cl>[CH:1]1([NH:7][S:19]([C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][CH:17]=[CH:18][C:9]=3[Cl:8])[CH:14]=2)(=[O:20])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

6

반응물 4

HCID 7965Cyclohexylamine2회HCID 81531DiisopropylethylamineHCID 2210045-Chloronaphthalene-1-sulphonyl chlorideHCID 27357775-Chloronaphthalene-2-sulphonyl chloride

생성물 1

HCID 19708732N-Cyclohexyl-5-chloro-2-naphthalenesulfonamide

시약·촉매·용매 1

HCID 6212
Chloroform
용매
2회

실험 절차

The title compound was prepared from the coupling of cyclohexylamine and 5-chloro-2-naphthalenesulfonyl chloride. Cyclohexylamine (1.0 g, 3.8 mmol) and diisopropyl ethylamine (1.35 ml, 7.7 mmol) were dissolved in 30 ml chloroform. 5-Chloro-1-naphthalenesulfonyl chloride (0.88 m., 7.7 mmol) in 20 ml chloroform was added dropwise to the solution. After stirring overnight, the CHCl3 solution was washed with saturated sodium bicarbonate solution and brine. Drying over magnesium sulfate and evaporation of the CHCl3 followed by recrystallization with isopropyl ether/methanol gave 0.92 g (75% yield) of a yellow solid: mp 133°-134° C.; 1H NMR (CDCl3): 8.48 (d, J=1.8, 1 H, H1), 8.38 (d, J=9.0, 1 H, H3), 8.00 (d, J=9.0, 1 H, H4), 7.88 (d, J=8.3, 1 H, H6), 7.71 (d, J=7.5, 1 H, H8), 7.51 (t, J=7.8, 1 H, H7), 5.07 (d, J=7.7, 1 H, NH), 3.23-3.15 (m, 1 H, NHCH, 1.77-1.72 (m, 2 H, ring H's), 1.61-1.55 (m, 2H, ring H's), 1.51-1.45 (m, 1H, ring H), 1.22-1.10 (m, 6H ring H's); anal. calcd. for C16H18NO2SCl; C, 59.34; H, 5.60; N, 4.33; found: C, 59.27; H, 5.60; N, 4.30.

후처리

  1. washthe CHCl3 solution was washed with saturated sodium bicarbonate solution and brine
  2. dry with materialDrying over magnesium sulfate and evaporation of the CHCl3
  3. customfollowed by recrystallization with isopropyl ether/methanol

출처 및 근거

ORD 기록
ord-f03f65b779d6433d893954be703db7aa
출처 데이터셋
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05707985

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