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

HRID 602005

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HRID 602005 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 6212Chloroform용매2회

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온도
60 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-9c87c08183054d25addd37cb2ab63ce0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902400B2

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