Water → 5-undecyl-1h-1,2,4-triazol-3-amine

HRID 2081650Notes

Reaction equation

HRID 2081650 reaction equation
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].[C:10](O)(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].O>C1(C)C=CC=CC=1.CN(C)C1C=CC=CC=1>[NH2:8][C:7]1[N:9]=[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10])[NH:5][N:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3893Lauric AcidHCID 178513185HCID 178513185, compound

Product 1

HCID 2923235-undecyl-1h-1,2,4-triazol-3-amineYield 49.1%

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A slurry of aminoguanidine bicarbonate (8.0 g, 59 mmol), dodecanoic acid (11.8 g, 59 mmol), and N,N-dimethylaniline (0.1 mL, 0.8 mmol) in toluene (100 mL) was heated under reflux with the azeotropic removal of water (72 hours). The resulting slurry was cooled (25° C.) and concentrated in vacuo. The residue was partitioned between ethyl acetate (300 mL) and saturated sodium bicarbonate (300 mL). The aqueous layer was back extracted with ethyl acetate, and the combined organics were washed with brine (1×250 mL), then dried (MgSO4), and concentrated in vacuo. The resulting solid was dissolved in hot chloroform and chromatographed on silica (first ethyl acetate, then 90:10 chloroform:methanol). The product containing fractions were combined and concentrated in vacuo to yield 6.9 g (49.1%) of 3-amino 5-undecyl-1H-1,2,4-triazole as an off-white powder, m.p. 128.5°-132.0° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (300 mL) and saturated sodium bicarbonate (300 mL)
  3. extractionThe aqueous layer was back extracted with ethyl acetate
  4. washthe combined organics were washed with brine (1×250 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting solid was dissolved in hot chloroform
  8. customchromatographed on silica (first ethyl acetate
  9. additionThe product containing fractions
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04d41334d4fa4e74bba3b7254c054e04
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

Loading…