Potassium Carbonate → HCID 136147412, compound

HRID 868905Notes

Reaction equation

HRID 868905 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH2:22])=[O:21])=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH2:13][CH2:14][C:15]3[NH:22][C:20](=[O:21])[C:19]4[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:17]=3)[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4399936HCID 4399936, compoundHCID 178418822HCID 178418822, compound

Product 1

HCID 136147412HCID 136147412, compoundYield 5.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-phenyl-1H-imidazole (500 mg, 3.47 mmol), 2-(3-chloropropanamido)benzamide (1.17 g, 5.21 mmol) and K2CO3 (717 mg, 5.20 mmol) in DMF (50 mL) was stirred at 110° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (200 mL) and extracted with EtOAc (100 mL×3). The organic layer was dried over Na2SO4, filtered and concentrated. The resulting product was washed with EtOAc and filtered to give the desired product (60 mg). LC-MS: m/z 317 (M+H+).

Workup

  1. extractionextracted with EtOAc (100 mL×3)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe resulting product was washed with EtOAc
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2bcc012a5bf6456b98656fd19d2f9e81
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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