1H-1,2,4-Triazole → HCID 13326950, compound

HRID 652081Notes

Reaction equation

HRID 652081 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].CS(O[CH2:13][C:14]1([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15]1)(=O)=O>CN(C)C=O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:14]2([CH2:13][N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[CH2:17][CH2:16][CH2:15]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 13366833HCID 13366833, compound

Product 1

HCID 13326950HCID 13326950, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4.1 g of 1,2,4-triazole in 15 ml of N,N-dimethylformamide were added to 0.66 g of sodium hydride (80% strength dispersion in mineral oil) in 15 ml of N,N-dimethylformamide at room temperature, under nitrogen. The mixture was stirred for 30 minutes, after which 5.1 g of [1-(4-chlorophenyl)-cyclobut-1-yl]-methyl methanesulfonate in 15 ml of N,N-dimethylformamide were added dropwise, and the mixture was stirred for 24 hours at room temperature and for 12 hours at 100° C., then hydrolyzed with water and extracted with ethyl acetate. 2.6 g of 1-(4-chlorophenyl)-1-(1,2,4-triazol-1-ylmethyl)-cyclobutane of melting point 124°-125° C. were obtained.

Workup

  1. stirringthe mixture was stirred for 24 hours at room temperature and for 12 hours at 100° C.
  2. extractionhydrolyzed with water and extracted with ethyl acetate

Sources & evidence

ORD record
ord-eff1ac0ca88e47c9b56b8c754013c3de
Source dataset
uspto-grants-1987_06
Patent number
US04670454

Reaction notes

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