Sodium Hydroxide → 5-[(2-Cyanoaziridin-1-yl)methyl]thiophene-2-carboxylic acid
Reaction equation
[OH-].[Na+].[C:3]([CH:5]1[CH2:7][N:6]1[CH2:8][C:9]1[S:13][C:12]([C:14]([O:16]C)=[O:15])=[CH:11][CH:10]=1)#[N:4]>CC(C)=O>[C:3]([CH:5]1[CH2:7][N:6]1[CH2:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1)#[N:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
95 ml. 0.1 N Aqueous sodium hydroxide solution are added dropwise, with stirring, to 2.1 g. 2-cyano-1-(5-methoxycarbonyl-2-thenyl)-aziridine (see Example 13a) in 21 ml. acetone. When no more ester can be detected by thin layer chromatography, the reaction mixture is evaporated in a vacuum, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The evaporation residue is crystallized with diethyl ether. There is obtained 1.2 g (61% of theory) 2-cyano-1-(5-carboxy-2-thenyl)-aziridine; m.p. 108°-111° C. The sodium salt melts with decomposition at 238°-243° C.