N~1~-Ethyl-4-fluorobenzene-1,2-diamine → 1-ethyl-5-fluoro-2-methylbenzimidazole

HRID 2231263Notes

Reaction equation

HRID 2231263 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[NH2:11])[CH3:2].[CH2:12](C(CC)(CC)C([O-])([O-])[O-])[CH3:13]>C(O)C>[CH2:1]([N:3]1[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=2[N:11]=[C:12]1[CH3:13])[CH3:2]

Participants

4

Reactant 2

HCID 21286303N~1~-Ethyl-4-fluorobenzene-1,2-diamineHCID 21875354Triethylorthoaceate

Product 1

HCID 27743771-ethyl-5-fluoro-2-methylbenzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.92 g of N-ethyl-4-fluorophenylenediamine in 15 ml of ethanol was added 3.49 ml of triethylorthoacetate and the reaction refluxed for 6 hours. The solvent was removed and the residue partitioned between ethyl acetate and water. The organic phase was separated, dried and the solvent removed to give 2.87 g of product as a brown oil.

Workup

  1. temperaturethe reaction refluxed for 6 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-62923b89039e4f66ab900a6a4998885a
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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