Hydrochloric Acid → HCID 178439669, compound

HRID 2292219Notes

Reaction equation

HRID 2292219 reaction equation
[OH:1][C:2]1[C:3]([CH2:27][CH2:28][CH3:29])=[C:4]([CH:15]=[CH:16][C:17]=1[C:18](=[O:26])[C:19]1C=[CH:23][CH:22]=[CH:21][C:20]=1O)[O:5][CH2:6][C:7]1C=CC(C#N)=CC=1.C([Sn]([N:43]=[N+:44]=[N-:45])(CCCC)CCCC)CCC.[N-:46]=[N+]=[N-].Cl.[CH3:50][OH:51]>O1CCCC1.C(OCC)(=O)C.O>[OH:51][C:50]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:18]([C:17]1[CH:16]=[CH:15][C:4]([O:5][CH2:6][C:7]2[NH:46][N:43]=[N:44][N:45]=2)=[C:3]([CH2:27][CH2:28][CH3:29])[C:2]=1[OH:1])=[O:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 33558AzideHCID 4984872Tributyltin azideHCID 14421666HCID 14421666, compound

Product 1

HCID 178439669HCID 178439669, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

A mixture of 2.5 g of 4-([3-hydroxy-4-(2-hydroxybenzoyl)-2-propylphenoxy]methyl)benzonitrile and 7.98 g of tri n-butylstannylazide in 50 ml of tetrahydrofuran were heated at reflux for 3 days. An additional 2.66 g of the azide reagent were added and the reaction was heated at reflux for an additional 4 days. The reaction was cooled and 10 ml of a 10:1 methanol/1N hydrochloric acid mixture were added. After stirring for 1 hour, the mixture was poured into an ethyl acetate/water mixture and the layers were separated. The organic layer was washed once with water and once with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated in vacuo. The resulting oil was purified by high pressure liquid chromatography eluting with a 40-75% ethyl acetate in hexane gradient containing 0.5% acetic acid. The appropriate fractions were combined, evaporated, and crystallized from ethyl acetate/hexane to provide 1.72 g of the desired title product, m.p. 186°-187° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 3 days
  3. temperaturethe reaction was heated
  4. temperatureat reflux for an additional 4 days
  5. temperatureThe reaction was cooled
  6. customthe layers were separated
  7. washThe organic layer was washed once with water and once with a saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe resulting oil was purified by high pressure liquid chromatography
  12. washeluting with a 40-75% ethyl acetate in hexane gradient
  13. additioncontaining 0.5% acetic acid
  14. customevaporated
  15. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8be74ee25147444f922d9267d0a20d97
Source dataset
uspto-grants-1989_01
Patent number
US04801616

Reaction notes

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