2,6-Lutidine → 5-Amino-N-(triethylsilyl)-1H-1,2,4-triazole-3-carboxamide

HRID 1931544Notes

Reaction equation

HRID 1931544 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([C:7]([NH2:9])=[O:8])[NH:4][N:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])(=O)=O>ClCCCl.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]=[C:5]([C:7]([NH:9][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:8])[NH:4][N:3]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 187074943-amino-1H-1,2,4-triazole-5-carboxamide(SALTDATA: FREE)

Product 1

HCID 593125935-Amino-N-(triethylsilyl)-1H-1,2,4-triazole-3-carboxamideYield 26.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 3-amino-1H-1,2,4-triazole-5-carboxamide (103 mg, 0.810 mol) in 1,2-dichloroethane (1.62 mL) treated at room temperature with 2,6-lutidine (283 μL, 2.43 mmol) and triethylsilyl trifluoromethanesulfonate (458 μL, 2.03 mmol). After 22 hours the reaction was heated at 50° C. and after 1.5 hours of heating the reaction was allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (25 mL), dried over magnesium sulfate, filtered, and evaporated to an oil which was flash chromatographed (silica gel, 0-10% ethyl acetate:hexane) to give the title compound as a white solid (130 mg).

Workup

  1. temperatureof heating the reaction
  2. temperatureto cool to room temperature
  3. washwashed with water (25 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customchromatographed (silica gel, 0-10% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-5fb4753ee4434cab8649ff79e66580bc
Source dataset
uspto-grants-2012_05
Patent number
US08188085B2

Reaction notes

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