1H-1,2,4-Triazole, 1-methyl- → HCID 68842365, compound

HRID 1948616Notes

Reaction equation

HRID 1948616 reaction equation
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1.[CH3:12][NH:13][C:14]1(C#N)[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1>O1CCCC1>[CH3:12][NH:13][C:14]1([C:11]2[N:7]([CH3:6])[N:8]=[CH:9][N:10]=2)[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 224591H-1,2,4-Triazole, 1-methyl-HCID 28899027HCID 28899027, compoundHCID 178418339Butyllithium

Product 1

HCID 68842365HCID 68842365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Butyllithium (2.5 M in hexane, 9.2 ml, 23.0 mmole) was added to a reaction vessel under an argon atmosphere and cooled to −78° C. 1-methyl-1,2,4-triazole (1.30 ml, 23 mmole) was dissolved in absolute tetrahydrofuran (60.0 ml) and added dropwise at −78° C. while cooling with ice. The reaction mixture was then stirred for 10 minutes at this temperature. 8-methylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (2.12 g, 10.8 mmole) in absolute tetrahydrofuran (15 ml) in a cooling bath maintained at −78° C. was then quickly added dropwise to the formed solution. After the addition the reaction solution was stirred for 1 hour in the cooling bath and was then slowly heated to 0° C. The reaction mixture was stirred overnight at room temperature. The mixture was then hydrolysed at 0° C. with water (10 ml), the aqueous phase was extracted with chloroform (3×50 ml), and the organic phase was washed with water (50 ml) and saturated NaCl solution (50 ml), dried over Na2SO4 and concentrated by evaporation in vacuo. The product was purified by means of flash chromatography with chloroform/methanol (15:1).

Workup

  1. additionadded dropwise at −78° C.
  2. temperaturewhile cooling with ice
  3. additionwas then quickly added dropwise to the formed solution
  4. additionAfter the addition the reaction solution
  5. stirringwas stirred for 1 hour in the cooling bath
  6. temperaturewas then slowly heated to 0° C
  7. stirringThe reaction mixture was stirred overnight at room temperature
  8. extractionhydrolysed at 0° C. with water (10 ml), the aqueous phase was extracted with chloroform (3×50 ml)
  9. washthe organic phase was washed with water (50 ml) and saturated NaCl solution (50 ml)
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated by evaporation in vacuo
  12. customThe product was purified by means of flash chromatography with chloroform/methanol (15:1)

Sources & evidence

ORD record
ord-d35306bfe8f845cbafbc17481824e4dc
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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