1H-1,2,4-Triazole → HCID 178442552, compound

HRID 582176Notes

Reaction equation

HRID 582176 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[PH:23](=[O:26])([OH:25])[OH:24].[CH2:27]([C:29]([CH2:57][CH3:58])([CH:31](Br)[C:32]1[N:36]=[CH:35][N:34]([C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:33]=1)[CH3:30])[CH3:28]>CN(C)C=O.O>[PH:23](=[O:24])([OH:26])[OH:25].[CH2:27]([C:29]([CH2:57][CH3:58])([CH:31]([N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)[C:32]1[N:36]=[CH:35][N:34]([C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:33]=1)[CH3:30])[CH3:28]

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 178442503HCID 178442503, compound

Product 1

HCID 178442552HCID 178442552, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1,2,4-triazole (0.15 g) in dry N,N-dimethyl-formamide (10 ml) was treated, under nitrogen, with sodium hydride (0.075 g, 60% in oil) and 15-Crown-5 (0.02 g). After ten minutes, the stirred mixture was treated with diethyl 3-bromo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 29). After a further three hours, it was poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure, finally at 0.01 mm. The residue was chromatographed on silica, using dichloromethane-ethanol (19:1) as eluant, to give diethyl 3(1,2,4-triazol-1-yl)-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.39 g) as a colourless oil. NMR (CDCl3): δ 1.2(6H,dt), 1.7-1.8(2H,m), 2.6-2.8(2H,m), 4.05(4H,m), 5.7(1H,t), 7.1(6H,m), 7.3(9H,m), 7.95(2H,2 xs), 8.25(1H,s). M/S: M+ 556.

Workup

  1. waitAfter ten minutes
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure, finally at 0.01 mm
  6. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-0015b2f58bd549fc9b4f169fa558c307
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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