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

HRID 1953986ノート

反応式

HRID 1953986 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-01cb2d31b3d9435aae9bd6034aeed38d
出典データセット
uspto-grants-2000_09
特許番号
US06121201

反応ノート

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