Water → HCID 22921554, compound

HRID 2258613Notes

Reaction equation

HRID 2258613 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[C:10]([N+:14]([O-])=O)[C:11]([F:13])=[CH:12][C:7]=2[N:6]=[C:5]1[C:17]([F:20])([F:19])[F:18])[C:2]#[CH:3].C(OCC)(=O)C.O>C(O)(=O)C.[Fe]>[CH2:1]([N:4]1[C:8]2[CH:9]=[C:10]([NH2:14])[C:11]([F:13])=[CH:12][C:7]=2[N:6]=[C:5]1[C:17]([F:19])([F:20])[F:18])[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 22921582HCID 22921582, compound

Product 1

HCID 22921554HCID 22921554, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 1.5 grams (0.005 mole) of 1-(2-propyn-1-yl)-2-trifluoromethyl-5-fluoro-6-nitrobenzimidazole, 1.0 gram (0.018 mole) of iron powder, and 10 mL of ethyl acetate in 35 mL of acetic acid was heated at 60° C. for two hours. The reaction mixture was then poured into water, and the mixture was extracted thoroughly with portions of ethyl acetate. The combined extracts were washed with aqueous solutions saturated with sodium bicarbonate and sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil, which was triturated with water, and the resultant solid collected by filtration. The solid was dried, yielding 1.3 grams of 1-(2-propyn-1-yl)-2-trifluoromethyl-5-fluoro-6-aminobenzimidazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionthe mixture was extracted thoroughly with portions of ethyl acetate
  2. washThe combined extracts were washed with aqueous solutions saturated with sodium bicarbonate and sodium chloride
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual oil, which
  6. customwas triturated with water
  7. filtrationthe resultant solid collected by filtration
  8. customThe solid was dried

Sources & evidence

ORD record
ord-0f2a9c035f514969a37494e3a6c550a6
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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