1H-1,2,4-Triazole → alpha-n-butyl-alpha-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-propanenitrile

HRID 1902841Notes

Reaction equation

HRID 1902841 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[Na].N1C=NC=N1.[OH-].[Na+].[C:14]([C:16]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17]Br)#[N:15]>O.CS(C)=O>[C:14]([C:16]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)#[N:15]

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 13069853HCID 13069853, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 13069855alpha-n-butyl-alpha-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-propanenitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide solution (25 ml) of sodium 1,2,4-triazole, generated from 3.2 g (0.046 m) of 1H-1,2,4-triazole and 1.85 g (0.046 m) of sodium hydroxide, is added 2-cyano-2-(2,4-dichlorophenyl) hexyl bromide dropwise at 110°. The whole is stirred at 110° for 11/2 hours. The reaction mixture is poured into 400 ml of water and extracted with ether. The combined ether extracts are washed with water and dried over MgSO4. Drying agent was filtered and to the filtrate is added conc. nitric acid dropwise until no more precipitates form. The precipitate (8.0 g) is filtered and is characterized as the nitric acid salt (RH 45,136) of the desired product.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed with water
  3. dry with materialdried over MgSO4
  4. customDrying agent
  5. filtrationwas filtered and to the filtrate
  6. additionis added conc. nitric acid dropwise until
  7. customno more precipitates form
  8. filtrationThe precipitate (8.0 g) is filtered

Sources & evidence

ORD record
ord-f62562969a85421fa06225451b220993
Source dataset
uspto-grants-1982_12
Patent number
US04366165

Reaction notes

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