Hydrochloric Acid → HCID 178470518, compound

HRID 2379470Notes

Reaction equation

HRID 2379470 reaction equation
[C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])#[N:2].FC(F)(F)C(O)=O.[N-:15]=[N+:16]=[N-:17].[Na+].Cl>N1C=CC=CC=1>[NH:15]1[C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:2][N:17]=[N:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 69336Ethyl cyanoformate

Product 1

HCID 178470518HCID 178470518, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred, room temperature solution of ethyl cyanoformate (19.57 g, 0.1975 mol) in pyridine (78 mL) was added a chilled (+5° C.) mixture of trifluoroacetic acid (33 mL) and pyridine (118 mL) followed by sodium azide (14.06 g, 0.2163 mol), and the mixture was heated at 60° C. for 46 hours. The mixture was allowed to cool, poured into a mixture of concentrated hydrochloric acid (180 mL) and ice (400 g), and extracted with ethyl acetate several times. The extracts were washed with saturated sodium chloride, dried (MgSO4), and rotoevaporated to an oil. The oil was chromatographed on silica gel (500 g, 70-230 mesh) using ethyl acetatemethanol (15:1, 10×1 L) as eluent. Fractions containing product were rotoevaporated to an oil. The oil was dissolved in chloroform, filtered to remove a precipitate, and the filtrate extracted with aqueous sodium hydroxide. The extracts were acidified to pH 1 and extracted with ethyl acetate. The extracts were dried (MgSO4) and rotoevaporated to a white solid, yield 1.91 g (7%) of the title compound, mp=87.5°-91.5° C.

Workup

  1. temperaturea chilled
  2. temperatureto cool
  3. extractionextracted with ethyl acetate several times
  4. washThe extracts were washed with saturated sodium chloride
  5. dry with materialdried (MgSO4)
  6. customThe oil was chromatographed on silica gel (500 g, 70-230 mesh)
  7. additionFractions containing product
  8. dissolutionThe oil was dissolved in chloroform
  9. filtrationfiltered
  10. customto remove a precipitate
  11. extractionthe filtrate extracted with aqueous sodium hydroxide
  12. extractionextracted with ethyl acetate
  13. dry with materialThe extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-50c02f47ab7a429eb39d9a83e1d3c523
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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