Dimethylformamide → HCID 178439680, compound

HRID 978127Notes

Reaction equation

HRID 978127 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH:9](C)[CH2:10][CH2:11][CH2:12][C:13]#N)=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].[CH3:28][N:29](C)C=O>>[OH:21][C:5]1[C:6]([CH2:18][CH2:19][CH3:20])=[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:28]2[NH:29][N:24]=[N:23][N:22]=2)[CH:16]=[CH:17][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 20204661HCID 20204661, compound

Product 1

HCID 178439680HCID 178439680, compound

Procedure

A mixture of 13.70 g 5-(4-acetyl-3-hydroxy-2-propylphenoxy)hexane-nitrile, 9.30 g sodium azide, 7.65 g ammonium chloride in 275 mL anhydrous dimethylformamide was stirred and heated at 120° for 90 hr. An additional 3.10 g of sodium azide and 2.57 g of ammonium chloride were added after 54 hr. The solvent was removed in vacuo and the residual solid was treated with 350 mL of water and acidified with 7 mL of 6N hydrochloric acid. The product was extracted with ethyl acetate and the dried (magnesium sulfate) extract was concentrated in vacuo to give an oil which was purified by high pressure liquid chromatography. Elution with toluene (70):ethyl acetate (25):acetic acid (10) gave a solid which was recrystallized from acetone-hexane. Filtration gave 8.55 g, mp 98°-100°, of 1-[2-hydroxy-3-propyl-4-[5-1H-tetrazol-5-yl)pentyloxy]phenyl ethanone. A second crop of 1.80 g, mp 94°-97°, was obtained.

Workup

  1. temperatureheated at 120° for 90 hr
  2. customThe solvent was removed in vacuo
  3. additionthe residual solid was treated with 350 mL of water
  4. extractionThe product was extracted with ethyl acetate
  5. dry with materialthe dried (magnesium sulfate)
  6. extractionextract
  7. concentrationwas concentrated in vacuo
  8. customto give an oil which
  9. customwas purified by high pressure liquid chromatography
  10. washElution with toluene (70)
  11. customethyl acetate (25):acetic acid (10) gave a solid which
  12. customwas recrystallized from acetone-hexane
  13. filtrationFiltration
  14. customgave 8.55 g, mp 98°-100°
  15. customA second crop of 1.80 g, mp 94°-97°, was obtained

Sources & evidence

ORD record
ord-9822c82de0a946179fb3f406769ecd24
Source dataset
uspto-grants-1987_05
Patent number
US04663332

Reaction notes

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