Potassium Carbonate → HCID 178510659, compound

HRID 1464580Notes

Reaction equation

HRID 1464580 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[C:3]=1[O:4][C:5]1[CH:14]=[CH:13][C:8]([NH:9][CH2:10][C:11]#[N:12])=[C:7]([N+:15]([O-])=[O:16])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:11]([C:10]1[NH:9][C:8]2[CH:13]=[CH:14][C:5]([O:4][C:3]3[C:18]([F:26])=[CH:19][C:20]([C:22]([F:24])([F:23])[F:25])=[CH:21][C:2]=3[Cl:1])=[CH:6][C:7]=2[N+:15]=1[O-:16])#[N:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19086746HCID 19086746, compound

Product 1

HCID 178510659HCID 178510659, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)-2-nitro-N-cyanomethylaniline (1 g) was suspended in hot ethanol (50cm3) and anhydrous potassium carbonate (0.18 g) added. The mixture was then stirred under reflux for 4 hours and left at room temperature overnight. The solvent was evaporated from the mixture under vacuum and the residue dissolved in water (75cm3), filtered and acidified with 2M hydrochloric acid. The yellow precipitate was collected and washed with water, then hexane and air dried to give 2-cyano-5-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)-1H-benzimidazole-3-oxide (0.8 g). M+ =370.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solvent was evaporated from the mixture under vacuum
  3. dissolutionthe residue dissolved in water (75cm3)
  4. filtrationfiltered
  5. customThe yellow precipitate was collected
  6. washwashed with water
  7. dry with materialhexane and air dried

Sources & evidence

ORD record
ord-58c29442273347a4979c9836ee885b1d
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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