Hydroxyamine hydrochloride → N-Hydroxy-3-[3-(naphthalen-1-ylsulfamoyl)-phenyl]-acrylamide

HRID 351060ノート

反応式

HRID 351060 の反応式
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[C:9]1([NH:19][S:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31](Cl)=[O:32])[CH:26]=[CH:27][CH:28]=2)(=[O:22])=[O:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>O1CCCC1>[OH:3][NH:2][C:31](=[O:32])[CH:30]=[CH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([S:20](=[O:22])(=[O:21])[NH:19][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[CH:24]=1

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 739894023-[3-(Naphthalen-1-ylsulfamoyl)phenyl]-acryloyl Chloride

生成物 1

HCID 85325510N-Hydroxy-3-[3-(naphthalen-1-ylsulfamoyl)-phenyl]-acrylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of hydroxylamine hydrochloride (0.215 g, 3.1 mmol) in tetrahydrofuran (3.5 ml) a saturated NaHCO3 solution (2.7 ml) was added and the resultant mixture was stirred at ambient temperature for 10 min. To the reaction mixture a solution of crude 3-[3-(naphthalen-1-ylsulfamoyl)phenyl]-acryloyl chloride (16d) (0.23 g) in tetrahydrofuran (2.5 ml) was added and the mixture was stirred at ambient temperature for one hour. The reaction mixture was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water and saturated NaCl, then the solvent was removed. The residue was crystallised from ethyl acetate affording the title compound (0.054 g, 24%). M.p. 180° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.45 (1H, d, J=16.0 Hz); 7.14 (1H, dd, J=7.0 and 1.4 Hz); 7.31–8.14 (11H, m); 9.09 (1H, br s); 10.27 (1H, s); 10.76 (1H, br s). HPLC analysis on Symmetry C18 column: impurities 4% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 40:60; sample concentration 0.3 mg/ml; flow rate 1.2 ml/min; detector UV 220 nm). Anal. Calcd for C19H16N2O4S, %: C, 61.94; H, 4.38; N, 7.60. Found, %: C, 61.18; H, 4.32; N, 7.54.

後処理

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water and saturated NaCl
  4. customthe solvent was removed
  5. customThe residue was crystallised from ethyl acetate affording the title compound (0.054 g, 24%)

出典と根拠

ORDレコード
ord-fdec900102fa46928186b08ed4d4eca4
出典データセット
uspto-grants-2007_02
特許番号
US07183298B2

反応ノート

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