Sulfuric Acid → 2-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanamide

HRID 257725Notes

Reaction equation

HRID 257725 reaction equation
[CH2:1]([C:5]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)([CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)[C:6]#[N:7])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)[OH:22]>[OH-].[NH4+]>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:5]([CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([NH2:7])=[O:22])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 6336Myclobutanil

Product 1

HCID 199569562-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanamideYield 56.5%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a 500 mL flask was charged 75.0 g (0.24 mole) of alpha-n-butyl-alpha-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile followed by 300 mL of 95% sulfuric acid. The mixture was stirred at 90° C. for 7 days after which the mixture was cooled to room temperature, diluted with ice and neutralized with ammonium hydroxide until basic (pH 8). The product was extracted with ethylene dichloride then washed with water and dried over magnesium sulfate. The solvent was concentrated and gave 45 g (56.5% yield) of a solid, Example 157 of Table 1.

Workup

  1. temperaturewas cooled to room temperature
  2. extractionThe product was extracted with ethylene dichloride
  3. washthen washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-85a28dfa14d2475f85072ea786fec312
Source dataset
uspto-grants-1993_11
Patent number
US05264415

Reaction notes

Loading…