Acetic acid, azido-, ethyl ester → HCID 86183871, compound

HRID 1957022Notes

Reaction equation

HRID 1957022 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[N:14]([CH2:17][C:18]([O:20][CH2:21]C)=[O:19])=[N+:15]=[N-:16].C[O-].[Na+]>CO.[Cl-].[Na+].O>[N:14]([C:17](=[CH:10][C:9]1[CH:12]=[CH:13][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1)[C:18]([O:20][CH3:21])=[O:19])=[N+:15]=[N-:16]

Participants

6

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 86183871HCID 86183871, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a cooled (0° C.) solution of 4-(1-imidazolyl)benzaldehyde (1.41 g, 8.16 mol) and ethyl azidoacetate (10.6 g, 81.7 mmol) in MeOH (50 ml) under nitrogen atmosphere is added sodium methoxide (28 wt. % solution in MeOH, 13,2 ml, 65 mmol) dropwise. Stirring is continued for 1.5 h. Then, the reaction mixture is diluted with brine (100 ml) and extracted with three portions of ether. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give methyl 2-azido-3-[4-(1-imidazolyl)phenyl]-2-propenate.

Workup

  1. extractionextracted with three portions of ether
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bcf69ae73f04cbcb2b9bd7ee7f34dd5
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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