Ammonium Chloride → HCID 57445718, compound

HRID 602006Notes

Reaction equation

HRID 602006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][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-:22].[NH4+]>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[Cl:22][CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[NH:8][C:6](=[O:7])[C:5]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]#[CH:21])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57701139HCID 57701139, compound

Product 1

HCID 57445718HCID 57445718, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent2×

Procedure

A mixture of 2 ml of chloroform and 224 mg of zinc (II) chloride was stirred at room temperature for 5 minutes. Then, a mixture of 235 mg of 7-[3-methoxy-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 washed with hexane to obtain 0.25 g of N-(2-chlorocyclohexyl)-3-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 108 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
  6. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-95992f29b6224dd39323218e08b58a51
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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