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

HRID 725777
ノート
印刷プレビュー

反応式

HRID 725777 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7965Cyclohexylamine2 回HCID 81531DiisopropylethylamineHCID 2210045-Chloronaphthalene-1-sulphonyl chlorideHCID 27357775-Chloronaphthalene-2-sulphonyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f03f65b779d6433d893954be703db7aa
出典データセット
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05707985

反応ノート

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