Hydrochloric Acid → 3-Azidomethyl-2-thienylacetic Acid
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureunder reflux for 5 hours
- extractionthe mixture is extracted with ether
- extractionThe product is then extracted into ether
- dry with materialThe ether is dried
- customevaporated
- 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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