Hydrochloric Acid → Ethyl 5-(aminomethyl)-1,3,4-oxadiazole-2-carboxylate

HRID 966424Notes

Reaction equation

HRID 966424 reaction equation
C(OC([NH:8][CH2:9][C:10]1[O:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][N:11]=1)=O)(C)(C)C.Cl.C(Cl)Cl.C(OCC)(=O)C>O1CCOCC1>[NH2:8][CH2:9][C:10]1[O:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10084542Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylateHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 11378755Ethyl 5-(aminomethyl)-1,3,4-oxadiazole-2-carboxylateYield 8.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Crude, unpurified compound 8 (5 g) is added portionwise to a 0° C. commercially available solution of hydrogen chloride in 1,4-dioxan (Aldrich, 4 M, 35 ml.) Compound 8a slowly dissolves to afford a clear yellow solution. After stirring for approximately 12 hours, the reaction mixture turns cloudy. TLC on silica using methylene chloride:ethyl acetate (9:1) as the eluent shows the starting material has been consumed. The reaction mixture is filtered and a white solid is obtained. The solid is washed exhaustively with ether (50 mL) to afford 266 mg of compound 9.

Workup

  1. dissolutionslowly dissolves
  2. customto afford a clear yellow solution
  3. customhas been consumed
  4. filtrationThe reaction mixture is filtered
  5. customa white solid is obtained
  6. washThe solid is washed exhaustively with ether (50 mL)

Sources & evidence

ORD record
ord-9345db7ae7524d01b9cf14030e24a32f
Source dataset
uspto-grants-2005_10
Patent number
US06951946B2

Reaction notes

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