Ammonium Chloride → HCID 54228975, compound

HRID 1683282Notes

Reaction equation

HRID 1683282 reaction equation
[Na].[N:2]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:3]=[N-:4].[CH3:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[CH:21]=O)=[CH:15][CH:14]=1.[NH4+].[Cl-]>C(O)C>[N:2]([C:5](=[CH:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([O:17][C:16]2[CH:26]=[CH:27][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:19]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:3]=[N-:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 1235533-(4-Methoxyphenoxy)benzaldehydeHCID 5360545Sodium

Product 1

HCID 54228975HCID 54228975, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-5 °C

Procedure

Sodium metal (2.01 g, 87.43 mmol) cut into small pieces was dissolved in absolute ethanol (67 mL) and the resulting solution cooled to -5° C. A mixture of ethyl azidoacetate (11.32 g, 87.67 mmol) and 3-(4-methoxyphenoxy) benzaldehyde (5.0 g, 21.91 mmol) was added dropwise over 30 min. On completion of addition the mixture was stirred at -5° C. for 4.5 hr, and then kept at room temperature overnight. The red reaction mixture was poured into saturated aqueous NH4Cl solution and extracted (3×) with Et2O. The ethereal extracts were washed (H2O and then saturated aqueous NaCl), dried (MgSO4) and evaporated to give an orange gum which was chromatographed (silica gel; hexane/Et2O; 0-15%). The product: ethyl 2-azido-3-(3-(4-methoxyphenoxy)phenyl)propenoate, was thus obtained as a light yellow gum, 5.5 g (70%).

Workup

  1. additionwas added dropwise over 30 min
  2. additionOn completion of addition the mixture
  3. waitkept at room temperature overnight
  4. customThe red reaction mixture
  5. extractionextracted (3×) with Et2O
  6. washThe ethereal extracts were washed (H2O
  7. dry with materialsaturated aqueous NaCl), dried (MgSO4)
  8. customevaporated
  9. customto give an orange gum which
  10. customwas chromatographed (silica gel; hexane/Et2O; 0-15%)

Sources & evidence

ORD record
ord-b4fc940c4eaa4104942af7626388e17f
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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