Sodium Bicarbonate → N-(4-(5-amino-1,3,4-thiadiazol-2-yl)-1,2,5-oxadiazol-3-yl)-2,2,2-trifluoroacetamide

HRID 1371548Notes

Reaction equation

HRID 1371548 reaction equation
[C:1]([C:3]1[C:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:5][O:6][N:7]=1)#[N:2].N[NH:16][C:17]([NH2:19])=[S:18].C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[NH2:19][C:17]1[S:18][C:1]([C:3]2[C:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:5][O:6][N:7]=2)=[N:2][N:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723789ThiosemicarbazideHCID 21071304N-(4-cyano-1,2,5-oxadiazol-3-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 21071303N-(4-(5-amino-1,3,4-thiadiazol-2-yl)-1,2,5-oxadiazol-3-yl)-2,2,2-trifluoroacetamideYield 51%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a suspension of N-(4-cyano-1,2,5-oxadiazol-3-yl)-2,2,2-trifluoroacetamide (0.10 g, 0.49 mmol) in 2 mL of TFA was added thiosemicarbazide (0.044 g, 0.49 mmol). The reaction mixture was poured into ice and neutralized with sat. NaHCO3 to pH=7. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with NaCl and concentrated. Trituration with diethyl ether afforded the title compound as a beige solid (0.070 g, 51%). 1H NMR (DMSO, 500 MHz) δ 7.93 (s, 2H), 6.55 (s, 1H). Mass Spec. FIA MS 281.1(M+1).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  2. washThe combined organic layer was washed with NaCl
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d413def3779048aeb57fbb9a90a9c402
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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