Water → 4-(4-chloro-benzylsulfanyl)-3,5-dimethyl-1H-pyrazole

HRID 1797134ノート

反応式

HRID 1797134 の反応式
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][S:7][CH:8]([C:12](=O)[CH3:13])[C:9](=O)[CH3:10])=[CH:4][CH:3]=1.O.[NH2:18][NH2:19].O>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][S:7][C:8]2[C:12]([CH3:13])=[N:18][NH:19][C:9]=2[CH3:10])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 221748613-(4-Chloro-benzylsulfanyl)-pentane-2,4-dione

生成物 1

HCID 221748524-(4-chloro-benzylsulfanyl)-3,5-dimethyl-1H-pyrazole収率 72%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 702Ethanol溶媒

実験手順

To a solution of crude 3-(4-chloro-benzylsulfanyl)-pentane-2,4-dione [prepared as described above from 3-chloro-pentan-2,3-dione (1.03 g, 7.63 mmol) and 4-chlorobenzyl mercaptan (1.21 g, 7.63 mmol)] in ethanol (60 mL) was added hydrazine hydrate (0.713 mL, 22.9 mmol) and p-toluenesulfonic acid monohydrate (ca. 25 mg). The solution was heated to reflux and stirred for 15 hours. The reaction mixture was allowed to cool to room temperature, and water (300 mL) was added. The precipitate that formed was removed by filtration, washed with water, and dried to provide 1.38 g (72%) of the product as a white solid: 1H NMR (CDCl3) δ 7.17 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 3.57 (s, 2H), and 2.02 (s, 6H) ppm. 13C NMR (CDCl3) δ 137.2, 132.7, 130.3, 128.3, 105.2, 39.9, 10.7 ppm.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customThe precipitate that formed
  4. customwas removed by filtration
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-7853a5884ad1498a849305931e26e942
出典データセット
uspto-grants-2006_04
特許番号
US07034031B2

反応ノート

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