Sulfuric Acid → 2-(4-Chloro-2-fluoro-5-hydroxyphenyl)hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one

HRID 1017181ノート

反応式

HRID 1017181 の反応式
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:12]([O:13]C(C)C)=[CH:11][C:10]([N:17]2[C:25](=[O:26])[N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][N:19]3[C:18]2=[S:27])=[C:9]([F:28])[CH:8]=1>C(Cl)Cl>[Cl:6][C:7]1[C:12]([OH:13])=[CH:11][C:10]([N:17]2[C:25](=[O:26])[N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][N:19]3[C:18]2=[S:27])=[C:9]([F:28])[CH:8]=1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 1590081H-(1,2,4)Triazolo(1,2-a)pyridazin-1-one, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)hexahydro-3-thioxo-

生成物 1

HCID 133922772-(4-Chloro-2-fluoro-5-hydroxyphenyl)hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Conc. sulfuric acid (22 ml) was added dropwise to a solution of 2-[4-chloro-2-fluoro-5-(isopropyloxy)phenyl]hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one (17.2 g) in methylene chloride (120 ml) stirred at 0° C. The mixture was stirred at room temperature for 1 hour and ice-water (200 g) added. The aqueous phase was extracted with methylene chloride and the organic phases combined, dried over sodium sulfate and chromatographed (silica gel, ethyl acetate) to give the product (14.5 g, 96%). 1H NMR (CDCl3, TMS): 1.84(4H, m), 3.82(4H, m), 7.06(1H, d, J=6.5 Hz), 7.58(1H, d, J=8.8 Hz), 10.6(1H, s).

後処理

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionThe aqueous phase was extracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. customchromatographed (silica gel, ethyl acetate)

出典と根拠

ORDレコード
ord-e40b43423b0e45bcb0da1318f0e26a42
出典データセット
uspto-grants-2002_11
特許番号
US06479435B1

反応ノート

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