Hydrazoic acid → HCID 20204649, compound

HRID 978133Notes

Reaction equation

HRID 978133 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]([C:10]1[CH:35]=[CH:34][C:13]([O:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=2)[C:19]([NH:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=O)=[C:12]([CH2:36][CH2:37][CH3:38])[C:11]=1[OH:39])(=[O:9])[CH3:8].[NH:40]=[N+:41]=[N-:42].N=[N+]=[N-].C(Cl)(Cl)[Cl:47]>C(Cl)(Cl)Cl>[Cl:47][C:34]1[C:13]([O:14][CH2:15][C:16]2[CH:33]=[CH:32][CH:31]=[C:18]([C:19]3[N:21]([CH2:22][CH2:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[N:42]=[N:41][N:40]=3)[CH:17]=2)=[C:12]([CH2:36][CH2:37][CH3:38])[C:11]([OH:39])=[C:10]([C:7](=[O:9])[CH3:8])[CH:35]=1

Participants

6

Reactant 4

HCID 24530Hydrazoic acidHCID 24819Phosphorus pentachlorideHCID 13912812HCID 13912812, compoundHCID 86741477HCID 86741477, compound

Product 1

HCID 20204649HCID 20204649, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Phosphorus pentachloride (2.80 g) was added in portions to a stirred solution of 5.0 g 3-[(4-acetyl-3-hydroxy-2-propylphenoxy)methyl]-N-[3-(3-pyridinyl)propyl]benzamide in 100 mL of anhydrous chloroform at 3°. The reaction mixture was stirred at 3° for an additional 0.25 hr and 25° for 1.75 hr. To this yellow solution stirred at 25° was added dropwise 22 mL of 1.1M hydrazoic acid in chloroform. The reaction was stirred at 25° for 24 hr and then an additional 22.2 mL of 1.1M hydrazoic acid/chloroform solution was added. After stirring for 24 hr at 25° and refluxing for 10 hr, the reaction mixture was washed with saturated sodium bicarbonate solution, dried (magnesium sulfate) and concentrated in vacuo to an oil which was purified by high pressure liquid chromatography. Elution with triethylamine (1.5):ethyl acetate (98.5) gave 1-[5-chloro-2-hydroxy-3-propyl-4-[[3-[1-[3-(3-pyridinyl)propyl]-1H-tetrazol-5-yl]phenyl]methoxy]phenyl]ethanone.

Workup

  1. stirringTo this yellow solution stirred at 25°
  2. stirringThe reaction was stirred at 25° for 24 hr
  3. stirringAfter stirring for 24 hr at 25°
  4. temperaturerefluxing for 10 hr
  5. washthe reaction mixture was washed with saturated sodium bicarbonate solution
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo to an oil which
  8. customwas purified by high pressure liquid chromatography
  9. washElution with triethylamine (1.5)

Sources & evidence

ORD record
ord-11da7926f3324803be570371b1a1ff3e
Source dataset
uspto-grants-1987_05
Patent number
US04663332

Reaction notes

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