Trichloroacetic Acid → HCID 18369500, compound

HRID 1645908Notes

Reaction equation

HRID 1645908 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])[CH3:2].ClC(Cl)(Cl)C(O)=O.[N-:20]=[N+]=[N-].[Na+]>>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][NH:20][C:7]2=[O:12])[CH3:2]

Participants

4

Reactant 3

HCID 6421Trichloroacetic AcidHCID 33557Sodium AzideHCID 19802539HCID 19802539, compound

Product 1

HCID 18369500HCID 18369500, compoundYield 21.3%

Procedure

A mixture of 0.9 g (5.63 mmol) of 2,3-dihydro-4-ethyl-1H-inden-1-one and 20 g of trichloroacetic acid was heated at 60°-65° for 30 minutes. To this was added 2.5 g (38.3 mmol) of sodium azide and the mixture was heated at 60°-65°, under nitrogen, for 18 hours. It was poured into 200 ml of ice water and extracted with methylene chloride. The organic layer was washed with saturated sodium hydrogen carbonate, saturated sodium chloride, dried (MgSO4), and concentrated. The residue was chromatographed (SiO2) using a gradient from pure methylene chloride to 19:1 methylene chloride-methanol to give a solid which was rechromatographed using 98:1 methylene chloride-methanol. Recrystallization from toluene/hexane gave 0.21 g (21%) of product; mp 123°-126°.

Workup

  1. temperaturewas heated at 60°-65° for 30 minutes
  2. temperaturethe mixture was heated at 60°-65°, under nitrogen, for 18 hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with saturated sodium hydrogen carbonate, saturated sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed (SiO2)
  8. customto give a solid which
  9. customwas rechromatographed
  10. customRecrystallization from toluene/hexane

Sources & evidence

ORD record
ord-3b03f43c5e784f0e83b0cf36d0f20890
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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