1H-1,2,4-Triazole → HCID 19382009, compound

HRID 2209831Notes

Reaction equation

HRID 2209831 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.I[CH2:9][Si:10]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1.[NH4+].[Cl-]>CN(C=O)C>[CH2:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([Si:10]2([CH2:9][N:3]3[CH:7]=[N:6][CH:5]=[N:4]3)[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:20][CH:19]=1)[CH3:23]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19382025HCID 19382025, compound

Product 1

HCID 19382009HCID 19382009, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a 100 ml, round bottomed flask equipped with a condenser and a dropping funnel were added 0.29 g of NaH (0.01 mol, 80% dispersion in mineral oil) and 2 ml of DMF. After resolving 0.78 g (0.011 mol) of 1,2,4-triazole in 2 ml of dried DMF, the solution was added through the dropping funnel and the mixture was stirred for 15 min. 3.00 g (0.009 mol) of 1-iodomethyl-1-(4-ethoxyphenyl)-1-silacyclopentane as prepared in Example 9 was diluted with 3 ml of DMF to be dropwisely added to the flask, and the mixture was stirred at 45° C. for 4 and half hrs. After confirming by GC that all the reactants were participated with the reaction, the aqueous saturated NH4Cl solution was added therein, and the organic material was extracted three times 30 ml of diethylether. The extract was dried on anhydrous MgSO4, and filtered to remove the solvent The residue was separated by silica gel column (eluent: ether) to obtain 2.1 g of 1-(4-ethoxyphenyl)-1-(1H-1,2,4-triazole-1-yl) methyl-1-silacyclopentane.

Workup

  1. customTo a 100 ml, round bottomed flask equipped with a condenser and a dropping funnel
  2. additionthe solution was added through the dropping funnel
  3. additionto be dropwisely added to the flask
  4. stirringthe mixture was stirred at 45° C. for 4 and half hrs
  5. customwere participated with the reaction
  6. extractionthe organic material was extracted three times 30 ml of diethylether
  7. dry with materialThe extract was dried on anhydrous MgSO4
  8. filtrationfiltered
  9. customto remove the solvent The residue
  10. customwas separated by silica gel column (eluent: ether)

Sources & evidence

ORD record
ord-bb4c359d425c420bba85559a5a7cf5a8
Source dataset
uspto-grants-1995_10
Patent number
US05455356

Reaction notes

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