Ammonium Chloride → HCID 22671451, compound

HRID 1006442Notes

Reaction equation

HRID 1006442 reaction equation
[CH:1]1(Br)[CH2:3][CH2:2]1.[Mg].[CH2:6]([N:8]([CH2:27][CH3:28])[C:9]([C:11]1[CH:26]=[CH:25][C:14]([C:15]([C:17]2[CH:18]=[C:19]([O:23][CH3:24])[CH:20]=[CH:21][CH:22]=2)=[O:16])=[CH:13][CH:12]=1)=[O:10])[CH3:7].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([C:15]([C:14]2[CH:25]=[CH:26][C:11]([C:9](=[O:10])[N:8]([CH2:27][CH3:28])[CH2:6][CH3:7])=[CH:12][CH:13]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[OH:16])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 9995598N,N-Diethyl-4-(3-methoxybenzoyl)benzamide

Product 1

HCID 22671451HCID 22671451, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of cyclopropyl bromide (0.31 ml) dissolved in tetrahydrofuran (1.5 ml) was added with magnesium (46.9 mg) and stirred at 60° C. for 1 hour to prepare a Grignard reagent. The Grignard reagent was added with a solution of 3-(4-diethylcarbamoylbenzoyl)anisole (150 mg) synthesized in accordance with the method described in WO97/10230, which was dissolved in tetrahydrofuran (1.5 ml), and then stirred at 60° C. for 2 hours. The reaction mixture was added with saturated aqueous ammonium chloride (4 ml) with ice cooling to terminate the reaction and then extracted twice with dichloromethane (4 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1→1:1) to obtain 90.9 mg of the title compound. Yield: 53%.

Workup

  1. customsynthesized in accordance with the method
  2. stirringstirred at 60° C. for 2 hours
  3. customto terminate
  4. customthe reaction
  5. extractionextracted twice with dichloromethane (4 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-d70df8e30e494bdfb0af6f44d1770d6a
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

Loading…