3,4,6-Trifluorobenzene-1,2-diamine → HCID 18537794, compound

HRID 412728Notes

Reaction equation

HRID 412728 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[NH2:11].C(O[C:15]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=N)C>C(O)C>[F:8][C:7]1[C:2]2[N:1]=[C:15]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:11][C:3]=2[C:4]([F:10])=[C:5]([F:9])[CH:6]=1

Participants

4

Reactant 2

HCID 5956243,4,6-Trifluorobenzene-1,2-diamineHCID 13451607Ethyl 2-ethoxycarbonimidoylpropionate

Product 1

HCID 18537794HCID 18537794, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-diamino-3,4,6-trifluorobenzene (1.92 g, 11.8 mmol), ethyl 2-ethoxycarbonimidoylpropionate (3.1 g, 14.7 mmol) and absolute ethanol (6 ml) was heated at reflux until no further progression of the reaction was indicated by TLC indicated the reaction was not progressing further, filtered from NH4Cl and concentrated. The residue was purified by chromatography on silica (hexane: methylene chloride: ethyl acetate, 5:5:1) to give ethyl 2-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)propionate (1.37 g, 42%) as a tan crystalline solid; NMR (CDCl3): δ 10.35 (s, ½H), δ 7.05 (s, ½H), 6.7 (m, 1H), δ 4.25 (dd, 2H), δ 4.15 (dd, 1H), δ 1.73 (d, 3H), δ 1.31 (t, 3H); M+ 272.9 (calcd for C12H11F3N2O2: 272.23).

Workup

  1. temperaturewas heated
  2. temperatureat reflux until no further progression of the reaction
  3. filtrationfiltered from NH4Cl
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica (hexane: methylene chloride: ethyl acetate, 5:5:1)

Sources & evidence

ORD record
ord-cbd479142c1c47c890fa64a146dcdc43
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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