Ammonium Chloride → HCID 57701194, compound

HRID 602007Notes

Reaction equation

HRID 602007 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:22][CH3:23])[C:17]=1[O:18][CH2:19][C:20]#[CH:21])[C:6]([N:8]1[CH:14]2[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:7].[Cl-:24].[NH4+]>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[Cl:24][CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[NH:8][C:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:17]([O:18][CH2:19][C:20]#[CH:21])=[C:16]([O:22][CH3:23])[CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57701202HCID 57701202, compound

Product 1

HCID 57701194HCID 57701194, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent2×

Procedure

A mixture of 2 ml of chloroform and 258 mg of zinc (II) chloride was stirred at room temperature for 5 minutes. Thereafter, a mixture of 300 mg of 7-[3,5-dimethoxy-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane and 2 ml of chloroform was added dropwise thereto at room temperature, and the resulting mixture was stirred at room temperature 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 0.16 g of N-(2-chlorocyclohexyl)-3,5-dimethoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 109 of the present invention) represented by the formula:

Workup

  1. additionwas added dropwise
  2. stirringat room temperature, and the resulting mixture was stirred at room temperature for 5 hours
  3. extractionthis was extracted with chloroform
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5700d92e6a9e48aab6382f4bd2487864
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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