1-Bromoundecane → HCID 10537926, compound

HRID 2081654Notes

Reaction equation

HRID 2081654 reaction equation
C[O-].[Na+].[Na].[NH2:5][C:6]1[N:10]=[CH:9][NH:8][N:7]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CO>[NH2:5][C:6]1[N:7]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[N:8]=[CH:9][N:10]=1.[NH2:5][C:6]1[N:10]=[CH:9][N:8]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[N:7]=1.[NH2:5][C:6]1[N:10]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[CH:9]=[N:8][N:7]=1

Participants

8

Reactant 4

HCID 127441-BromoundecaneHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 178418311HCID 178418311, compound

Product 3

HCID 10490141HCID 10490141, compoundYield 4.2%HCID 10537926HCID 10537926, compoundYield 18.7%HCID 10610009HCID 10610009, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A methanol solution of sodium methoxide was generated by dissolving sodium (2.06 g, 89.6 mmol) in methanol (300 mL). 3-Amino-1,2,4-triazole (7.5 g, 89.6 mmol) was added and the resulting solution was stirred (10 minutes, 25° C.). Undecylbromide (20.0 mL, 89.6 mmol) was then added and the resulting solution was heated under reflux for 24 hours. The resulting solution was cooled (25° C.) and concentrated in vacuo. The residue was taken up in ethyl acetate (450 mL), washed with brine (2×150 mL), then dried (MgSO4) and concentrated in vacuo. The resulting solid was dissolved in a minimal amount of chloroform and chromatographed on silica (98:2 chloroform:methanol) to yield 3.0 g (14.0%) of 3-amino-2-undecyl-1,2,4 -triazol (analysis for C13H26N4 : Calcd: C, 65.50; H, 10.99; N, 23.50; Found: C, 65.49; H, 10.98; N, 23.88), 4.0 g (18.7%) of 3-amino-1-undecyl-1,2,4-triazole (analysis for C13H26N4 : Calcd: C, 65.50; H, 10.99; N, 23.50; Found: C, 65.42; H, 10.93; N, 23.48), and 0.9 g (4.2%) of 3-amino-4-undecyl-1,2,4-triazole (analysis for C13H26N4 : Calcd: C, 65.50; H, 10.99; N, 23.50; Found: C, 65.20; H, 10.92; N, 23.52).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe resulting solution was cooled (25° C.)
  4. concentrationconcentrated in vacuo
  5. washwashed with brine (2×150 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting solid was dissolved in a minimal amount of chloroform
  9. customchromatographed on silica (98:2 chloroform:methanol)

Sources & evidence

ORD record
ord-7558f4790f61487abe3916a3712d3008
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

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