Ammonium Chloride → HCID 86753651, compound

HRID 361609Notes

Reaction equation

HRID 361609 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:7]=1[CH:8]=O.[N:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[N+:17]=[N-:18].[Cl-].[NH4+]>CO>[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:7]=1[C:8]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:7]=1)=[C:19]([N:16]=[N+:17]=[N-:18])[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 667262,5-DimethoxybenzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 86753651HCID 86753651, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

While 23 ml of sodium methoxide (28% solution in methanol) in 40 ml of anhydrous methanol was stirred vigorously, 40 ml of a mixed methanol solution containing 4.0 g (21.1 mmol) of 2,5-dimethoxybenzaldehyde and 9.7 g (84.2 mmol) of methyl azidoacetate was added dropwise at -15° C. After completion of the addition, the reaction mixture was stirred for 2 hours. Then the reaction mixture was poured into a saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to provide 3.1 g of methyl 2,5-dimethoxyphenyl-α-azidocinnamate.

Workup

  1. additionwas added dropwise at -15° C
  2. additionAfter completion of the addition
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d3b18866e13a4ceba6cb6fa906dbdb8c
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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