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

HRID 1708346

Reaction equation

HRID 1708346 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 melting point 197°-199° C.

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-ecca77b4f8fb49948b1249b2cabb9481
Source dataset
uspto-grants-1994_10
Patent number
US05358939

Linked notes

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