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

HRID 1064535노트

반응식

HRID 1064535 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ec7d7be2470c43a9b4aca07b7b550a45
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969728B2

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