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

HRID 966423Notes

Reaction equation

HRID 966423 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>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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10084542Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylate2×

Product 1

HCID 11378755Ethyl 5-(aminomethyl)-1,3,4-oxadiazole-2-carboxylateYield 93.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In an alternative procedure, compound 8 (33.3 g, 0.12 mol) is added portionwise to a 0° C. commercially available solution of hydrogen chloride in 1,4-dioxan (Aldrich, 4 M, 750 ml.) Compound 8 slowly dissolves to afford a clear yellow solution. After stirring for approximately 30 minutes, the reaction mixture turns cloudy. The starting material is consumed in about two hours, as determined by TLC on silica using methylene chloride:ethyl acetate (9:1) as the eluent. The reaction mixture is filtered and a colorless solid product is obtained. The solid is washed exhaustively with ether (1L) to afford 19.2 g (76%) of compound 9.

Workup

  1. dissolutionslowly dissolves
  2. customto afford a clear yellow solution
  3. customThe starting material is consumed in about two hours
  4. filtrationThe reaction mixture is filtered
  5. customa colorless solid product is obtained
  6. washThe solid is washed exhaustively with ether (1L)

Sources & evidence

ORD record
ord-61b94a6a7cc143f9afa0120c24b9b904
Source dataset
uspto-grants-2005_10
Patent number
US06951946B2

Reaction notes

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