Potassium Carbonate → HCID 19086745, compound

HRID 1464582Notes

Reaction equation

HRID 1464582 reaction equation
[C:1]([C:3]1[NH:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=3[Cl:24])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].Br[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[N:4]([CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:5]2[CH:11]=[C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([C:20]([F:22])([F:23])[F:21])=[CH:15][C:14]=3[Cl:24])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[C:1]([C:3]1[N:7]([CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:6]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([C:20]([F:22])([F:23])[F:21])=[CH:15][C:14]=3[Cl:24])=[CH:11][C:5]=2[N:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 19086710HCID 19086710, compound

Product 2

HCID 19086745HCID 19086745, compoundHCID 19086747HCID 19086747, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Cyano-5-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)benzimidazole (0.325 g), ethyl 2-bromopropionate (0.13cm3) and anhydrous potassium carbonate (1 g) were heated under reflux in acetonitrile (30cm3) for 2 hours and left at room temperature overnight. The mixture was filtered and the solvent removed from the filtrate under vacuum. The residue was purified by preparative plate chromatography (SiO2 ; hexane:ether,1:1) to yield ethyl 2-[2-cyano-6-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)benzimidazol-1-yl]-propionate (0.14 g) as the faster component (compound 101) and ethyl 2-[2-cyano-5-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)benzimidazol-1-yl]propionate (0.15 g) as the slower component (compound 100).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed from the filtrate under vacuum
  3. customThe residue was purified by preparative plate chromatography (SiO2 ; hexane:ether,1:1)

Sources & evidence

ORD record
ord-5ee0762d810748b885fd684198e0eb0a
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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