Ammonium Chloride → N-(2-chlorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide

HRID 602005

反応式

HRID 602005 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:21])[C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:5]([N:7]1[CH:13]2[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]2)=[O:6].[Cl-:22].[NH4+]>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[Cl:22][CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[NH:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([F:1])[C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:15]([F:21])[CH:14]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 577011787-[3,5-Difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane

生成物 1

HCID 57701136N-(2-chlorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 6212Chloroform溶媒2 回

反応条件

温度
60 °C

実験手順

A mixture of 4 ml of chloroform and 298 mg of zinc (II) chloride was stirred at 60° C. After 5 minutes, a mixture of 291 mg of 7-[3,5-difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane and 2 ml of chloroform was added dropwise thereto at 60° C., and the resulting mixture was heated under reflux for 5 hours. Then, an aqueous saturated ammonium chloride solution was added to the reaction mixture, and this was extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.22 g of N-(2-chlorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 87 of the present invention) represented by the formula:

後処理

  1. additionwas added dropwise
  2. temperatureat 60° C., and the resulting mixture was heated
  3. temperatureunder reflux for 5 hours
  4. extractionthis was extracted with chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9c87c08183054d25addd37cb2ab63ce0
出典データセット
uspto-grants-2011_03
特許番号
US07902400B2

関連ノート

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