HCID 13621740, compound → HCID 13621746, compound

HRID 746090Notes

Reaction equation

HRID 746090 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)=[CH:5][CH:4]=1>CC(O)=O.Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[NH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 13621740HCID 13621740, compound

Product 1

HCID 13621746HCID 13621746, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of XIII (6.6 g, 0.035 mole) in glacial HOAc (40 mL) and 48% HBr (110 mL) was stirred at reflux for 7 hours and then evaporated to dryness in vacuo. The residue was stirred with saturated NaHCO3 (200 mL) for 16 hours at room temperature. The aqueous phase was decanted from the residue which again was stirred with saturated NaHCO3 for 2 hours. This aqueous phase was decanted and the residue was extracted with 3×100 mL of boiling H2O filtering from insoluble material. All of the aqueous phases were combined and evaporated to dryness in vacuo. The residue was extracted with 3×100 mL of CHCl3 --MeOH (60:40), filtering from inorganic material. Evaporation of the filtrate left the crude product as an oily brown solid that was purified by chromatography on silica gel, eluting with 90CHCl3 --10MeOH--1H2O; to yield XIV (74%); m.p. 188°-190° C. (CH3CN).

Workup

  1. temperatureat reflux for 7 hours
  2. customevaporated to dryness in vacuo
  3. customThe aqueous phase was decanted from the residue which
  4. stirringagain was stirred with saturated NaHCO3 for 2 hours
  5. customThis aqueous phase was decanted
  6. extractionthe residue was extracted with 3×100 mL of boiling H2O filtering from insoluble material
  7. customevaporated to dryness in vacuo
  8. extractionThe residue was extracted with 3×100 mL of CHCl3 --MeOH (60:40)
  9. filtrationfiltering from inorganic material
  10. customEvaporation of the filtrate
  11. waitleft the crude product as an oily brown solid that
  12. customwas purified by chromatography on silica gel
  13. washeluting with 90CHCl3 --10MeOH--1H2O

Sources & evidence

ORD record
ord-5c215e446a1047d4b26df6e4a5ceeb63
Source dataset
uspto-grants-1986_07
Patent number
US04602093

Reaction notes

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