Ammonium Chloride → Ethyl 2-azido-3-(5-methylthiophen-2-yl)acrylate

HRID 518123Notes

Reaction equation

HRID 518123 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[O-]CC.[Na+].[CH3:14][C:15]1[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1.[Cl-].[NH4+]>CO.O>[N:1]([C:4](=[CH:20][C:18]1[S:19][C:15]([CH3:14])=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 76601917Ethyl 2-azido-3-(5-methylthiophen-2-yl)acrylateYield 72.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl azidoacetate (10.6 g) in methanol (65 mL) was added sodium ethoxide (20% solution in ethanol, 27.2 g) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. 5-Methylthiophene-2-carbaldehyde (2.5 g) was added to this solution and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added saturated ammonium chloride aqueous solution and water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0−90/10) to give the title compound (3.39 g)

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0−90/10)

Sources & evidence

ORD record
ord-cc182f3ea8f94aaeb8e1da5b43927dd6
Source dataset
uspto-grants-2015_08
Patent number
US09115144B2

Reaction notes

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