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4-Toluenesulfonyl chloride → 4-{2-Chloro-4-[(5-chloro-6-methoxypyridin-2-yl)carbonyl]phenoxy}butyl 4-methylbenzenesulfonate

HRID 70501
ノート
印刷プレビュー

反応式

HRID 70501 の反応式
C(N(CC)CC)C.Cl.CN(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[Cl:24][C:25]1[CH:26]=[C:27]([C:37]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([O:46][CH3:47])[N:40]=2)=[O:38])[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36]>C(Cl)(Cl)Cl.O>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:36][CH2:35][CH2:34][CH2:33][CH2:32][O:31][C:30]2[CH:29]=[CH:28][C:27]([C:37]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([O:46][CH3:47])[N:40]=3)=[O:38])=[CH:26][C:25]=2[Cl:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chloride2 回HCID 8471Triethylamine2 回HCID 10313079Trimethylamine HydrochlorideHCID 67398017[3-Chloro-4-(4-hydroxybutoxy)phenyl](5-chloro-6-methoxypyridin-2-yl)methanone

生成物 1

HCID 584527454-{2-Chloro-4-[(5-chloro-6-methoxypyridin-2-yl)carbonyl]phenoxy}butyl 4-methylbenzenesulfonate収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

Triethylamine (830 μL), trimethylamine hydrochloride (188 mg) and 4-methylbenzenesulfonyl chloride (555 mg) were sequentially added to a solution of [3-chloro-4-(4-hydroxybutoxy)phenyl](5-chloro-6-methoxypyridin-2-yl)methanone obtained in Reference Example 1-34(1) (360 mg) in chloroform (8 mL) under ice-cooling, and the mixture was stirred at room temperature for 4.5 hours. Triethylamine (150 μL) and 4-methylbenzenesulfonyl chloride (185 mg) were sequentially added under ice-cooling, and the mixture was stirred at room temperature for further 1.5 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the title compound (357 mg, 70%).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for further 1.5 hours
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-efa0e8f8f6ed4ae795b91739cdb6e267
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

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