Sodium Azide → 2-Tetrahydrothiophenecarboxylic acid azide

HRID 1702795Notes

Reaction equation

HRID 1702795 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[S:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10](Cl)=[O:11]>O.C(OCC)C>[S:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([N:1]=[N+:2]=[N-:3])=[O:11]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 13778885Thiolane-2-carbonyl chloride

Product 1

HCID 544483672-Tetrahydrothiophenecarboxylic acid azideYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of sodium azide (4.14 g.) in water (16 ml.) was added dropwise to a solution of 2-tetrahydrothiophenecarboxylic acid chloride (9.60 g.) in diethyl ether (24 ml.) with stirring under ice-cooling and stirred for further 15 minutes at the same temperature. After the mixture was stirred for 1 hour at ambient temperature, nitrogen gas was introduced to remove off diethyl ether. The resultant mixture was extracted with diethyl ether (50 ml.). The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo to give oily 2-tetrahydrothiophenecarboxylic acid azide (8.63 g.).

Workup

  1. temperaturecooling
  2. stirringstirred for further 15 minutes at the same temperature
  3. stirringAfter the mixture was stirred for 1 hour at ambient temperature
  4. additionnitrogen gas was introduced
  5. customto remove off diethyl ether
  6. extractionThe resultant mixture was extracted with diethyl ether (50 ml.)
  7. washThe extracts were washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3590ab6abbec4ae8b1133662124d47a9
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

Loading…