Acetic acid, azido-, ethyl ester → HCID 59683351, compound

HRID 2206569Notes

Reaction equation

HRID 2206569 reaction equation
[S:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[N:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N+:9]=[N-:10].[Na]>C(O)C>[N:8](/[C:11](=[CH:6]\[C:5]1[S:1][CH:2]=[N:3][CH:4]=1)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N+:9]=[N-:10]

Participants

5

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 27735771,3-Thiazole-5-carbaldehydeHCID 5360545Sodium

Product 1

HCID 59683351HCID 59683351, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of thiazole-5-carbaldehyde (20 g, 176.77 mmol) and ethyl 2-azidoacetate (91.2 g, 707.1 mmol) in anhydrous ethanol (100 mL) was added sodium (16.26 g, 707.1 mmol) dissolved in anhydrous ethanol (1000 mL) dropwise between −10° C. and 0° C. After the addition, the mixture was stirred below 0° C. for 4 hours, and then warm to the ambient temperature and allowed to stir overnight. The reaction mixture was washed with saturated ammonium chloride, extracted with acetic ester (500 mL×3), the combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 20:1→10:1) to afford the title compound (9 g, 23%) as an yellow solid. LCMS (M+H+) m/z: calcd. 224.04. found 224.9.

Workup

  1. additionAfter the addition
  2. stirringto stir overnight
  3. washThe reaction mixture was washed with saturated ammonium chloride
  4. extractionextracted with acetic ester (500 mL×3)
  5. dry with materialthe combined organic phase was dried by anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by column chromatograph on silica gel
  9. washeluted with (petrol ether/acetic ester 20:1→10:1)

Sources & evidence

ORD record
ord-d5e777409d7b488c93c15dc6e09e158b
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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