Sodium Hydroxide → 5-[(2-Cyanoaziridin-1-yl)methyl]thiophene-2-carboxylic acid

HRID 647525Notes

Reaction equation

HRID 647525 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

HCID 14798Sodium HydroxideHCID 20483552HCID 20483552, compound

Product 1

HCID 204836075-[(2-Cyanoaziridin-1-yl)methyl]thiophene-2-carboxylic acidYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. customthe reaction mixture is evaporated in a vacuum
  2. extractionextracted with ethyl acetate
  3. customThe evaporation residue is crystallized with diethyl ether

Sources & evidence

ORD record
ord-285fa50b3c624a049a6a264a43facf9e
Source dataset
uspto-grants-1983_10
Patent number
US04409236

Reaction notes

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