Acetone → Methyl 3-Azidomethyl-2-thienyl Ketone

HRID 2420249Notes

Reaction equation

HRID 2420249 reaction equation
Br[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([CH3:10])=[O:9].CC(C)=O.[N-:15]=[N+:16]=[N-:17].[Na+]>O>[N:15]([CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([CH3:10])=[O:9])=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 217012741-[3-(Bromomethyl)thiophen-2-yl]ethan-1-one

Product 1

HCID 20381562Methyl 3-Azidomethyl-2-thienyl Ketone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 3-bromomethyl-2-thienyl ketone (5 g., 0.023 mole) in 42 ml. of acetone and 4 ml. of water was added sodium azide (1.56 g., 0.024 mole) with caution (exothermic!). The resulting solution was stirred at room temperature for 2.5 hours, the acetone evaporated, the residue diluted with water and extracted with diethyl ether. The combined extracts were washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfate and the dried extracts evaporated to dryness to obtain 4.0 g. (97%) of yellow oil. 1H--NMR (CDCl3), ppm. (δ): 7.5 (d, J=5, aromatic-H), 7.2 (d, J=5, aromatic-H), 4.75 (s, CH2N3), 2.5 (s, CH3); IR spectrum (film, cm.-1 : 3100, 2100 (N3), 1660, 1525 and 1420.

Workup

  1. customthe acetone evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe dried extracts evaporated to dryness
  7. customto obtain 4.0 g

Sources & evidence

ORD record
ord-1b88bccd4c9847f48245b472a7e1d562
Source dataset
uspto-grants-1978_08
Patent number
US04110342

Reaction notes

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