Ammonium Chloride → HCID 86601266, compound

HRID 853072Notes

Reaction equation

HRID 853072 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH:6]=O.[CH2:12]([O:14][C:15](=[O:20])[CH2:16][N:17]=[N+:18]=[N-:19])[CH3:13].[Cl-].[NH4+]>C(O)C.O.C(OCC)(=O)C>[CH2:12]([O:14][C:15](=[O:20])/[C:16](/[N:17]=[N+:18]=[N-:19])=[CH:6]/[C:5]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:3]([F:2])[CH:4]=1)[CH3:13]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 27745743-Fluoro-4-methylbenzaldehydeHCID 5360545Sodium2×

Product 1

HCID 86601266HCID 86601266, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To ethanol (200 ml) was added portionwise 6.7 g sodium metal in such a way that the temperature stayed below 50° C. After all sodium had dissolved, the temperature was brought to −5° C. and a solution of 3-fluoro-4-methylbenzaldehyde (10.0 g, 0.072 mol) and azido acetic acid ethyl ester (37.4 g, 0.29 mol) in 100 ml ethanol was added while maintaining the temperature below 5° C. After 3 h the orange-red solution was poured on saturated aqueous ammonium chloride solution and ethyl acetate (300 ml) and water (100 ml) was added. The phases were separated, the aqueous phase was reextracted three times with ethyl acetate (300 ml each) and the combined organic layers were washed with brine (400 ml) and dried over magnesium sulfate. The crude reaction product was purified by column chromatography over silical gel (0.030–0.063 mm) with n-hexane/tert-butyl methyl ether (50/1) as eluent to yield the title product as a yellow oil (9.8 g, 54.2%). EI-MS: m/e=249.1 (M)

Workup

  1. customstayed below 50° C
  2. customwas brought to −5° C.
  3. temperaturewhile maintaining the temperature below 5° C
  4. additionwas added
  5. customThe phases were separated
  6. washthe combined organic layers were washed with brine (400 ml)
  7. dry with materialdried over magnesium sulfate
  8. customThe crude reaction product
  9. customwas purified by column chromatography over silical gel (0.030–0.063 mm) with n-hexane/tert-butyl methyl ether (50/1) as eluent

Sources & evidence

ORD record
ord-f0d57bcb44394cb1aa98fdf3c92a72fa
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

Loading…