Hydrochloric Acid → 3-Azidomethyl-2-thienylacetic Acid

HRID 1448384Notes

Reaction equation

HRID 1448384 reaction equation
[N:1]([CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH2:10][C:11]([O:13]C)=[O:12])=[N+:2]=[N-:3].Cl>O1CCCC1>[N:1]([CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH2:10][C:11]([OH:13])=[O:12])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20381637Methyl 2-(3-azidomethyl-2-thienyl)acetate

Product 1

HCID 203113693-Azidomethyl-2-thienylacetic AcidYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.6 g. of the above ester in 200 ml. of tetrahydrofuran and 30 ml. of 3 N hydrochloric acid is heated under reflux for 5 hours. The cooled solution is then basified to pH 10 and the mixture is extracted with ether. The ether is discarded and the pH of the residual aqueous phase is lowered to 2. The product is then extracted into ether. The ether is dried and evaporated to give 10.5 g. (72% yield) of the acid as an oily solid.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionthe mixture is extracted with ether
  3. extractionThe product is then extracted into ether
  4. dry with materialThe ether is dried
  5. customevaporated
  6. customto give 10.5 g

Sources & evidence

ORD record
ord-b0d7a8655754436aa5d683d032c140a9
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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